Browse history interactively

Page 1

Page 1Revision 1

Page 2

Page 2Revision 2

← Previous editContent deleted Content addedVisualWikitext

Revision as of 12:41, 12 January 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to verified fields - updated 'ChEMBL_Ref') per Chem/Drugbox validation (report errors or bugs)← Previous edit		Latest revision as of 17:26, 2 January 2025 edit undoNavadda (talk | contribs)492 editsm →Production: formatting typoTags: Mobile edit Mobile app edit Android app edit App section source
Line 1:		Line 1:
			{{Short description|CHCl3, historical anaesthetic and common solvent}}{{other uses}}{{Use dmy dates|date=April 2023}}
	{{Fix bunching|beg}}
			{{Expand Turkish|Kloroform|date=September 2024|fa=yes}}
	{{chembox
			{{Chembox
	| Verifiedfields = changed
			|Verifiedimages = changed
	| verifiedrevid = 400138784
			|Watchedfields = changed
	| ImageFileL1 = Chloroform displayed.svg
			|verifiedrevid = 407464807
	| ImageSizeL1 =
			|ImageFileL1_Ref = {{chemboximage|correct|??}}
	| ImageFileR1 = Chloroform 3D.svg
			|ImageFileL1 = Chloroform_displayed.svg
	| ImageSizeR1 =
			|ImageClassL1 = skin-invert
	| IUPACName = Chloroform
			|ImageFileR1 = Chloroform-3D-balls.png
	| SystematicName = Trichloromethane
			|ImageFile2 = Chloroform_by_Danny_S._-_002.JPG
	| OtherNames = Formyl trichloride, Methane trichloride, Methyl trichloride, Methenyl trichloride, TCM, Freon 20, R-20, UN 1888
			|ImageName2 = Chloroform in its liquid state shown in a test tube
	| Section1 = {{Chembox Identifiers
			|ImageSize2 = 100px
	| UNII_Ref = {{fdacite|correct|FDA}}
			|PIN = Trichloromethane
	| UNII = 7V31YC746X
			|OtherNames = {{ubl|''Chloroformium''|Freon 20|Methane trichloride|Methyl trichloride|Methenyl trichloride|Methenyl chloride|Refrigerant-20|terchloride/perchloride of formyle<ref>Gregory, William, A Handbook of Organic Chemistry (Third edition corrected and much extended), 1852, page 177</ref><ref>Daniel Pereira Gardner, Medicinal Chemistry for the Use of Students and the Profession: Being a Manual of the Science, with Its Applications to Toxicology, Physiology, Therapeutics, Hygiene, Etc (1848), page 271</ref> ''(archaic)''|''Trichloretum Formylicum'' (])}}
	| InChIKey = HEDRZPFGACZZDS-UHFFFAOYAG
			|Section1 = {{Chembox Identifiers
	| ChEMBL_Ref = {{ebicite|changed|EBI}}
			|UNII_Ref = {{fdacite|correct|FDA}}
	| ChEMBL = 44618
			|UNII = 7V31YC746X
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			| Abbreviations = R-20, TCM
	| StdInChI = 1S/CHCl3/c2-1(3)4/h1H
			|InChIKey = HEDRZPFGACZZDS-UHFFFAOYAG
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
			|ChEMBL_Ref = {{ebicite|correct|EBI}}
	| StdInChIKey = HEDRZPFGACZZDS-UHFFFAOYSA-N
	| CASNo = 67-66-3		|ChEMBL = 44618
	| CASNo_Ref = {{cascite|correct|CAS}}		|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			|StdInChI = 1S/CHCl3/c2-1(3)4/h1H
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| ChemSpiderID = 5977
			|StdInChIKey = HEDRZPFGACZZDS-UHFFFAOYSA-N
	| EINECS = 200-663-8
	| PubChem = 6212		|CASNo = 67-66-3
			|CASNo_Ref = {{cascite|correct|CAS}}
	| ChEBI = 35255
			|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| KEGG = C13827
			|ChemSpiderID = 5977
	| SMILES = ClC(Cl)Cl
			|EINECS = 200-663-8
	| InChI = 1/CHCl3/c2-1(3)4/h1H
			|PubChem = 6212
	| RTECS = FS9100000
			| UNNumber = 1888
	}}
			|ChEBI_Ref = {{ebicite|correct|EBI}}
	| Section2 = {{Chembox Properties
			|ChEBI = 35255
	| Formula = CHCl<sub>3</sub>
			|KEGG_Ref = {{keggcite|correct|kegg}}
	| MolarMass = 119.38 g/mol
			|KEGG = C13827
	| Appearance = Colorless liquid
			|SMILES = ClC(Cl)Cl
	| Density = 1.483 g/cm<sup>3</sup>
			|InChI = 1/CHCl3/c2-1(3)4/h1H
	| MeltingPt = -63.5 °C
			|RTECS = FS9100000
	| BoilingPt = 61.2 °C
	| Solubility = 0.8 g/100 ml (20 °C)
	| RefractIndex = 1.4459
	}}
	| Section3 = {{Chembox Structure
	| CrystalStruct =
	| Coordination =
	| MolShape = Tetrahedral
	}}
	| Section7 = {{Chembox Hazards
	| MainHazards = Harmful ('''Xn'''), Irritant ('''Xi'''), ]
	| NFPA-H = 2
	| NFPA-F =
	| NFPA-R =
	| NFPA-O =
	| RPhrases = {{R22}}, {{R38}}, {{R40}}, {{R48/20/22}}
	| SPhrases = {{S2}}, {{S36/37}}
	| FlashPt = Non-flammable
	| Autoignition =
	| PEL = 50 ppm (240 mg/m<sup>3</sup>) (OSHA)
	}}
	}}		}}
			|Section2 = {{Chembox Properties
	{{Fix bunching|mid}}
			|C=1|H=1|Cl=3
	]
			|Appearance = Highly refractive colorless liquid
	{{Fix bunching|end}}
			|Odor = Sweet, minty, pleasant
			|Density = 1.564 g/cm<sup>3</sup> (−20&nbsp;°C)<br /> 1.489 g/cm<sup>3</sup> (25&nbsp;°C)<br /> 1.394 g/cm<sup>3</sup> (60&nbsp;°C)
			|MeltingPtC = −63.5
			|BoilingPtC = 61.15
			|BoilingPt_notes = <br /> decomposes at 450&nbsp;°C
			|VaporPressure = 0.62 kPa (−40&nbsp;°C)<br /> 7.89 kPa (0&nbsp;°C)<br /> 25.9 kPa (25&nbsp;°C)<br /> 313 kPa (100&nbsp;°C)<br /> 2.26 MPa (200&nbsp;°C)
			|Solubility = 10.62 g/L (0&nbsp;°C)<br /> 8.09 g/L (20&nbsp;°C)<br /> 7.32 g/L (60&nbsp;°C)
			|SolubleOther = Soluble in ]<br /> Miscible in ], ]s, ], ], ], ]
			|Solubility1 = ≥ 100 g/L (19&nbsp;°C)
			|Solvent1 = acetone
			|Solubility2 = ≥ 100 g/L (19&nbsp;°C)
			|Solvent2 = dimethyl sulfoxide
			|RefractIndex = 1.4459 (20&nbsp;°C)
			|LambdaMax = 250 nm, 260 nm, 280 nm
			|Viscosity = 0.563 cP (20&nbsp;°C)
			|pKa = 15.7 (20&nbsp;°C)
			|HenryConstant = 3.67 L·atm/mol (24&nbsp;°C)
			|ThermalConductivity = 0.13 W/(m·K) (20&nbsp;°C)
			|MagSus = −59.30·10<sup>−6</sup> cm<sup>3</sup>/mol
			}}
			|Section3 = {{Chembox Structure
			|MolShape = Tetrahedral
			|Dipole = 1.15 D
			}}
			|Section4 = {{Chembox Thermochemistry
			|HeatCapacity = 114.25 J/(mol·K)
			|Entropy = 202.9 J/(mol·K)
			|DeltaHf = −134.3 kJ/mol
			|DeltaGf = −71.1 kJ/mol
			|DeltaHc = 473.21 kJ/mol
			}}
			|Section6 = {{Chembox Pharmacology
			|ATCCode_prefix = N01
			|ATCCode_suffix = AB02
			}}
			|Section7 = {{Chembox Hazards
			|ExternalSDS =
			|Hazards_ref = <ref name= PubChem>{{cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/6212#section=Safety-and-Hazards|title=PubChem: Safety and Hazards – GHS Classification|publisher=National Center for Biotechnology Information, U.S. National Library of Medicine|access-date=17 August 2018|archive-date=17 August 2018|archive-url=https://web.archive.org/web/20180817125017/https://pubchem.ncbi.nlm.nih.gov/compound/6212#section=Safety-and-Hazards|url-status=live}}</ref>
			|MainHazards = Decomposes to extremely toxic ] and ] in presence of light – possibly carcinogenic – ] – hepatotoxic<ref>{{cite web|url=http://www.unece.org/fileadmin/DAM/trans/danger/publi/ghs/ghs_rev02/English/03e_part3.pdf|title=Part 3 Health Hazards|work=Globally Harmonized System of Classification and Labelling of Chemicals (GHS)|version=Second revised edition|publisher=United Nations|access-date=30 September 2017|archive-date=4 March 2019|archive-url=https://web.archive.org/web/20190304062207/http://www.unece.org/fileadmin/DAM/trans/danger/publi/ghs/ghs_rev02/English/03e_part3.pdf|url-status=live}}</ref><ref name=PGCH/><ref name=":1">Toxicity on {{Webarchive|url=https://web.archive.org/web/20180817125017/https://pubchem.ncbi.nlm.nih.gov/compound/6212#section=Toxicity |date=17 August 2018 }}</ref>
			|GHSPictograms = {{GHS06}} {{GHS08}} {{GHS corrosion}}
			|GHSSignalWord = Danger
			|HPhrases = {{H-phrases|302|315|319|331|336|351|361d|372}}
			|PPhrases = {{P-phrases|201|202|260|264|270|271|280|281|301+330+331|310|302+352|304+340|311|305+351+338|308+313|314|332+313|337+313|362|403+233|235|405|501}}
			|NFPA-H = 2
			|NFPA-F = 0
			|NFPA-R = 1
			|FlashPt = Nonflammable
			|PEL = 50 ppm (240 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0127}}</ref>
			|IDLH = 500 ppm<ref name=PGCH/>{{cln|reason=What is "ppm"??? Is it a mass/mass fraction, volume/volume fraction, mole/mole fraction, mass/volume fraction, and who knows what else??? Using ambiguous units like "ppm" without unambiguous explanation what that unit stands for irritates readers who are not experts in this field, and the readers have no power to read the writer's mind!|date=June 2023}}
			|REL = Ca ST 2 ppm (9.78 mg/m<sup>3</sup>) <ref name=PGCH/>
			|LD50 = 704 mg/kg (mouse, dermal)<ref>{{cite book |title=Sax's Dangerous Properties of Industrial Materials |edition=12th |year=2012 |last=Lewis |first=Richard J. |publisher=Wiley |isbn=978-0-470-62325-1}}</ref>
			|LC50 = 47,702 mg/m<sup>3</sup> (rat, 4 hr)<ref>{{cite web|url=https://www.epa.gov/sites/default/files/2016-09/documents/chloroform.pdf |title=Chloroform |date=September 2016 |website=Environmental Protection Agency |access-date=19 February 2024}}</ref>
			|LCLo = {{ubl|20,000 ppm (guinea pig, 2 hr)|7,056 ppm (cat, 4 hr)|25,000 ppm (human, 5 min)}}<ref name=IDLH>{{IDLH|67663|Chloroform}}</ref>{{cln|reason=What is "ppm"??? Is it a mass/mass fraction, volume/volume fraction, mole/mole fraction, mass/volume fraction, and who knows what else??? Using ambiguous units like "ppm" without unambiguous explanation what that unit stands for irritates readers who are not experts in this field, and the readers have no power to read the writer's mind!|date=June 2023}}
			}}
			|Section9 = {{Chembox Related
			|OtherFunction_label = chloromethanes
			|OtherCompounds = {{ubl|] {{chem2|CDCl3}}|] {{chem2|CH3Cl}}|] {{chem2|CH2Cl2}}|] {{chem2|CCl4}}|] {{chem2|CHF3}}|] {{chem2|CHBr3}}|] {{chem2|CHI3}}|] {{chem2|CHF2Cl}}|] {{chem2|CHFCl2}}|] {{chem2|CHCl2Br}}|] {{chem2|CHClBr2}}|] {{chem2|CHF2Br}}|] {{chem2|CHFBr2}}}}
			}}
			}}
			'''Chloroform''',<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 661 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4 | quote = The retained names 'bromoform' for HCBr<sub>3</sub>, 'chloroform' for HCCl<sub>3</sub>, and 'iodoform' for HCI<sub>3</sub> are acceptable in general nomenclature. Preferred IUPAC names are substitutive names.| chapter = Front Matter }}</ref> or '''trichloromethane''' (often abbreviated as '''TCM'''), is an ] with the ] {{chem2|CHCl3|auto=1}} and a common ]. It is a ], colorless, sweet-smelling, dense liquid produced on a large scale as a precursor to ]s and ].<ref name="Ullmann"> {{Ullmann|last=Rossberg|first=M.|display-authors=etal|title=Chlorinated Hydrocarbons|doi=10.1002/14356007.a06_233.pub2}}</ref> Chloroform was once used as an ] between the 19th century and the first half of the 20th century.<ref>{{cite web |url=http://www.history.com/topics/ether-and-chloroform |title=Ether and Chloroform |access-date=2018-04-24 |url-status=live |archive-url=https://web.archive.org/web/20180324191303/https://www.history.com/topics/ether-and-chloroform |archive-date=24 March 2018}}</ref><ref>{{Cite book | doi=10.1002/3527600418.mb6766e0014|chapter = Chloroform |title = The MAK-Collection for Occupational Health and Safety|pages = 20–58|year = 2012|isbn = 978-3-527-60041-0}}</ref> It is miscible with many solvents but it is only very slightly soluble in water (only 8 g/L at 20°C).
			==Structure and name==
			The molecule adopts a ] with C<sub>3v</sub> ].<ref>{{Cite web |title=Illustrated Glossary of Organic Chemistry - Chloroform |url=http://www.chem.ucla.edu/~harding/IGOC/C/chloroform.html |access-date=2022-12-29 |website=www.chem.ucla.edu}}</ref> The chloroform molecule can be viewed as a ] molecule with three hydrogen atoms replaced with three chlorine atoms, leaving a single hydrogen atom.
			The name "chloroform" is a ] of ''terchloride'' (tertiary chloride, a trichloride) and ''formyle'', an obsolete name for the ] radical (CH) derived from ].
			==Natural occurrence ==
			Many kinds of ] produce chloroform, and ] are believed to produce chloroform in soil.<ref>{{cite journal | last1 = Cappelletti | first1 = M. | year = 2012 | title = Microbial degradation of chloroform | journal = Applied Microbiology and Biotechnology | volume = 96 | issue = 6| pages = 1395–409 | doi = 10.1007/s00253-012-4494-1| pmid = 23093177 | s2cid = 12429523 }}</ref> Abiotic processes are also believed to contribute to natural chloroform productions in soils, although the mechanism is still unclear.<ref>{{cite journal | last1 = Jiao | first1 = Yi |display-authors=etal | year = 2018 | title = Halocarbon Emissions from a Degraded Forested Wetland in Coastal South Carolina Impacted by Sea Level Rise | journal = ACS Earth and Space Chemistry | volume = 2 | issue = 10 | pages = 955–967 | doi = 10.1021/acsearthspacechem.8b00044 | bibcode = 2018ESC.....2..955J | s2cid = 134649348 }}</ref>
			Chloroform is a volatile organic compound.<ref>{{cite web | url=http://aqt-vru.com/emissions/complete-list-of-vocs/ | title=Complete list of VOC's }}</ref>
			==History==
			Chloroform was synthesized independently by several investigators {{Circa|1831}}:
			*Moldenhawer, a German pharmacist from ], appears to have produced chloroform in 1830 by mixing ] with ]; however, he mistook it for ''Chloräther'' (chloric ether, ]).<ref>{{cite journal|last=Moldenhawer|date=1830|url=https://books.google.com/books?id=a_E3AAAAMAAJ&pg=PA222|title=Verfahren den Spiritus von dem Fuselöl auf leichte Weise zu befreien|trans-title=Procedure for freeing ethanol of fusel oil in an easy way|journal=Magazin für Pharmacie|volume=8|issue=31|pages=222–227|access-date=6 May 2016|archive-date=29 July 2020|archive-url=https://web.archive.org/web/20200729120000/https://books.google.com/books?id=a_E3AAAAMAAJ&pg=PA222|url-status=live}}</ref><ref>{{cite journal|last1=Defalque|first1=Ray J.|last2=Wright|first2=A. J. |title=Was chloroform produced before 1831?|journal=Anesthesiology|volume=92|issue=1|pages=290–291|pmid=10638939|year=2000|doi=10.1097/00000542-200001000-00060|doi-access=free}}</ref>
			*], a U.S. physician from ], also appears to have produced chloroform in 1831 by reacting chlorinated lime with ethanol, and noted its ] properties; however, he also believed that he had prepared chloric ether.<ref>{{cite journal|last=Guthrie|first=Samuel|year=1832|url=https://books.google.com/books?id=iuzRAAAAMAAJ&pg=PA64|title=New mode of preparing a spirituous solution of chloric ether|journal=The American Journal of Science and Arts|volume=21|pages=64–65 and 405–408|access-date=6 May 2016|archive-date=29 July 2020|archive-url=https://web.archive.org/web/20200729135541/https://books.google.com/books?id=iuzRAAAAMAAJ&pg=PA64|url-status=live}}</ref><ref>{{cite book|last=Guthrie|first=Ossian|date=1887|url=https://archive.org/details/39002011125375.med.yale.edu|page=|title=Memoirs of Dr. Samuel Guthrie, and the History of the Discovery of Chloroform|location=Chicago|publisher=George K. Hazlitt & Co.}}</ref><ref>{{cite book|last=Stratmann|first=Linda|date=2003|title=Chloroform: The Quest for Oblivion|location=Stroud|publisher=Sutton Publishing|chapter-url=https://books.google.com/books?id=VvA7AwAAQBAJ&pg=PT30|chapter=Chapter 2|isbn=978-0-7524-9931-4|access-date=6 May 2016|archive-date=29 July 2020|archive-url=https://web.archive.org/web/20200729120316/https://books.google.com/books?id=VvA7AwAAQBAJ&pg=PT30|url-status=live}}</ref>
			*] carried out the ] of ]. Liebig incorrectly states that the ] of chloroform was {{chem2|C2Cl5}} and named it "''Chlorkohlenstoff''" ("carbon chloride").<ref>{{cite journal|last=Liebig|first=Justus von|url=https://babel.hathitrust.org/cgi/pt?id=uc1.a0002753747;view=1up;seq=462|doi=10.1002/andp.18310991111|title=Ueber die Zersetzung des Alkohols durch Chlor|journal=Annalen der Physik und Chemie|volume=99|issue=11|page=444|trans-title=On the decomposition of alcohol by chlorine|year=1831|bibcode=1831AnP....99..444L|access-date=6 May 2016|archive-date=10 May 2017|archive-url=https://web.archive.org/web/20170510154137/https://babel.hathitrust.org/cgi/pt?id=uc1.a0002753747;view=1up;seq=462|url-status=live}}</ref><ref>{{cite journal|last=Liebig |first=Justus von |url=https://babel.hathitrust.org/cgi/pt?id=wu.89048351662&view=1up&seq=861 |year=1832|title=Ueber die Verbindungen, welche durch die Einwirkung des Chlors auf Alkohol, Aether, ölbildendes Gas und Essiggeist entstehen|journal=Annalen der Physik und Chemie |volume=100 |issue=2 |pages=243–295 |trans-title=On the compounds which arise by the reaction of chlorine with alcohol , ether , oil-forming gas , and spirit of vinegar |doi=10.1002/andp.18321000206|bibcode=1832AnP...100..243L }}<br />On pages 259–265, Liebig describes ''Chlorkohlenstoff'' ("carbon chloride", chloroform), but on p. 264, Liebig incorrectly states that the ] of chloroform is C<sub>2</sub>Cl<sub>5</sub>.</ref>
			*] obtained the compound by the action of ] on both ] and ].<ref>{{cite journal |last=Soubeiran |first=Eugène |date=1831 |url=https://babel.hathitrust.org/cgi/pt?id=ien.35556014127963;view=1up;seq=115 |title=Recherches sur quelques combinaisons du chlore |trans-title=Investigations into some compounds of chlorine |journal=Annales de Chimie et de Physique |series=Série 2 |volume=48 |pages=113–157 |access-date=6 May 2016 |archive-date=10 May 2017 |archive-url=https://web.archive.org/web/20170510154147/https://babel.hathitrust.org/cgi/pt?id=ien.35556014127963;view=1up;seq=115 |url-status=live }}
			*Reprinted in {{cite journal |last=Soubeiran |first=Eugène |date=1831 |url=https://books.google.com/books?id=QP1BAAAAcAAJ&pg=PA657 |title=Recherches sur quelques combinaisons du chlore |trans-title=Investigations on some compounds of chlorine |journal=Journal de Pharmacie et des Sciences Accessoires |volume=17 |pages=657–672 |access-date=6 May 2016 |archive-date=29 July 2020 |archive-url=https://web.archive.org/web/20200729112744/https://books.google.com/books?id=QP1BAAAAcAAJ&pg=PA657 |url-status=live }}
			*Reprinted in {{cite journal |last=Soubeiran |first=Eugène |date=1832 |url=https://books.google.com/books?id=aBZJAQAAMAAJ&pg=PA1 |title=Suite des recherches sur quelques combinaisons du chlore |trans-title=Continuation of investigations on some compounds of chlorine |journal=Journal de Pharmacie et des Sciences Accessoires |volume=18 |pages=1–24 |access-date=6 May 2016 |archive-date=29 July 2020 |archive-url=https://web.archive.org/web/20200729121309/https://books.google.com/books?id=aBZJAQAAMAAJ&pg=PA1 |url-status=live }}</ref>
			In 1834, French chemist ] determined chloroform's empirical formula and named it:<ref>{{cite journal|last=Dumas |first=J.-B. |date=1834 |title=Récherches rélative à l'action du chlore sur l'alcool |trans-title=Experiments regarding the action of chlorine on alcohol |journal=L'Institut, Journal Général des Sociétés et Travaux Scientifiques de la France et de l'Étranger |volume=2 |pages=106–108 and 112–115}}
			*Reprinted in {{cite journal|url=https://babel.hathitrust.org/cgi/pt?id=umn.31951d00316736l;view=1up;seq=668|title=Untersuchung über die Wirkung des Chlors auf den Alkohol|journal=Annalen der Physik und Chemie|volume=107|issue=42|pages=657–673|trans-title=Investigation of the action of chlorine on alcohol|doi=10.1002/andp.18341074202|bibcode=1834AnP...107..657D|year=1834|last1=Dumas|first1=J.-B.|access-date=12 May 2016|archive-date=10 May 2017|archive-url=https://web.archive.org/web/20170510152609/https://babel.hathitrust.org/cgi/pt?id=umn.31951d00316736l;view=1up;seq=668|url-status=live}}<br />On p. 653, Dumas states chloroform's empirical formula:
			::''"Es scheint mir also erweisen, dass die von mir analysirte Substance, … zur Formel hat: {{chem2|C2H2Cl6}}."'' (Thus it seems to me to show that the substance analyzed by me … has as formula: {{chem2|C2H2Cl6}}.)
			:Dumas then notes that chloroform's simple ] resembles that of ]. Furthermore, if chloroform is boiled with ], one of the products is ]. On p. 654, Dumas names chloroform:
			::''"Diess hat mich veranlasst diese Substanz mit dem Namen 'Chloroform' zu belegen."'' (This caused me to bestow this substance with the name "chloroform" .)
			*Reprinted in {{cite journal |doi=10.1002/jlac.18350160213 |url=https://babel.hathitrust.org/cgi/pt?id=uva.x002457902;view=1up;seq=542 |title=Ueber die Wirkung des Chlors auf den Alkohol |journal=Annalen der Pharmacie |volume=16 |issue=2 |pages=164–171 |trans-title=On the action of chlorine on alcohol |year=1835 |last1=Dumas |first1=J.-B. |access-date=12 May 2016 |archive-date=10 May 2017 |archive-url=https://web.archive.org/web/20170510152601/https://babel.hathitrust.org/cgi/pt?id=uva.x002457902;view=1up;seq=542 |url-status=live }}</ref> "''Es scheint mir also erweisen, dass die von mir analysirte Substanz, … zur Formel hat: C<sub>2</sub>H<sub>2</sub>Cl<sub>6</sub>.''" (Thus it seems to me to show that the substance I analyzed … has as formula: C<sub>2</sub>H<sub>2</sub>Cl<sub>6</sub>.). ... "''Diess hat mich veranlasst diese Substanz mit dem Namen 'Chloroform' zu belegen.''" (This had caused me to impose the name "chloroform" upon this substance .)
			In 1835, Dumas prepared the substance by alkaline cleavage of ].
			In 1842, ] in London discovered the anaesthetic qualities of chloroform on laboratory animals.<ref name=pdf1>{{cite journal|pmid=15023112|url=http://www.ph.ucla.edu/epi/snow/anaesthesia59_394_400_2004.pdf|year=2004|last1=Defalque|first1=R. J.|title=The short, tragic life of Robert M. Glover|journal=Anaesthesia|volume=59|issue=4|pages=394–400|last2=Wright|first2=A. J.|doi=10.1111/j.1365-2044.2004.03671.x|s2cid=46428403|url-status=live|archive-url=https://web.archive.org/web/20160309080158/http://www.ph.ucla.edu/epi/snow/anaesthesia59_394_400_2004.pdf|archive-date=9 March 2016|doi-access=free}}</ref>
	'''Chloroform''' is the ] with ] ]]]<sub>3</sub>. The colorless, sweet-smelling, dense liquid is a ], and is considered somewhat hazardous. Several million tons are produced annually as a precursor to ] and refrigerants, but its use for refrigerants is being phased out.<ref name=Ullmann>M. Rossberg ''et al.'' “Chlorinated Hydrocarbons” in Ullmann’s Encyclopedia of Industrial Chemistry, 2006, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a06_233.pub2}}</ref>
			In 1847, Scottish obstetrician ] was the first to demonstrate the anaesthetic properties of chloroform, provided by local pharmacist ] of Duncan, Flockhart and company,<ref name="Gordon2002" /> in humans, and helped to popularize the drug for use in medicine.<ref name=eb>{{cite encyclopedia|title=Sir James Young Simpson|url=https://www.britannica.com/EBchecked/topic/545447/Sir-James-Young-Simpson-1st-Baronet|encyclopedia=Encyclopædia Britannica|access-date=23 August 2013|url-status=live|archive-url=https://web.archive.org/web/20130727130133/https://www.britannica.com/EBchecked/topic/545447/Sir-James-Young-Simpson-1st-Baronet|archive-date=27 July 2013}}</ref>
	==Occurrence==
	CHCl<sub>3</sub> has a multitude of natural sources, both biogenic and abiotic. It is estimated that greater than 90% of atmospheric CHCl<sub>3</sub> is of natural origin.<ref>http://www.eurochlor.org/upload/documents/document56.pdf</ref>
			By the 1850s, chloroform was being produced on a commercial basis. In Britain, about 750,000 doses a week were being produced by 1895,<ref>{{Cite journal|last=Worling|first=P.M.|date=1998|title=Duncan and Flockhart: the Story of Two Men and a Pharmacy|journal=Pharmaceutical Historian|volume=28|issue=2|pages=28–33|pmid=11620310}}</ref> using the Liebig procedure, which retained its importance until the 1960s. Today, chloroform – along with ] – is prepared exclusively and on a massive scale by the chlorination of methane and chloromethane.<ref name="Ullmann"/>
	===Marine===
	In particular, chloroform is produced by brown seaweeds ('']'', '']'', '']'', '']'', '']''), red seaweeds (''Gigartina stellata'', '']'', ''] lanosa''), and green seaweeds ('']'', '']'' sp., ''] albida'').<ref>{{Cite journal|author=Nightingale PB, Malin G, Liss PS|year=1995|url=http://www.jstor.org/pss/2838303|title=Production of Chloroform and Other Low- Molecular-Weight Halocarbons by Some Species of Macroalgae|journal=Limnology and Oceanography|volume=40|page=680|issue=4|publisher=American Society of Limnology and Oceanography}}</ref> Similarly, the macroalga ''Eucheuma denticulatum'', which is cultivated and harvested on a large scale for ] production, produces CHCl<sub>3</sub>,<ref>{{Cite journal|doi=10.1080/09670269600651241|title=Stress-induced production of volatile halogenated organic compounds in Eucheuma denticulatum (Rhodophyta) caused by elevated pH and high light intensities|year=1996|last1=Mtolera|first1=Matern|last2=Collén|first2=Jonas|last3=Pedersén|first3=Marianne|last4=Ekdahl|first4=Anja|last5=Abrahamsson|first5=Katarina|last6=Semesi|first6=Adelaida|journal=European Journal of Phycology|volume=31|pages=89 }}</ref> as do ''Hypnea spinella'', ''Falkenbergia hillebrandii'', and ''Gracilara cornea'' along with seven indigenous macroalgae inhabiting a rock pool.<ref>{{Cite journal|author=Ekdahl A, Pedersen M, Abrahamsson K|year=1998|title=A Study of the Diurnal Variation of Biogenic Volatile Halocarbons|journal= Mar Chem|volume=63|page=1}}</ref> These studies show increased CHCl<sub>3</sub> production with increased light intensity, presumably when photosynthesis is at a maximum. Chloroform is also produced by the brown alga '']'', the green algae ''Cladophora glomerata'', ''Enteromorpha ahlneriana'', ''] flexuosa'', and ''Enteromorpha intestinalis'', and the diatom ''Pleurosira laevis''.<ref>{{Cite journal|doi=10.1016/S0031-9422(03)00419-9|pmid=13679095|year=2003|last1=Abrahamsson|first1=K|last2=Choo|first2=KS|last3=Pedersén|first3=M|last4=Johansson|first4=G|last5=Snoeijs|first5=P|title=Effects of temperature on the production of hydrogen peroxide and volatile halocarbons by brackish-water algae.|volume=64|issue=3|pages=725–34|journal=Phytochemistry}}</ref> Other studies observe CHCl<sub>3</sub> in '']'', ''Fucus vesiculosis'', ''Corallina officinalis'', ''Cladophora pellucida'', and ''Ulva lactuca'',<ref>{{Cite journal|author=Baker JM, Sturges WT, Sugier J, Sunnenberg G, Lovett AA, Reeves CE, Nightingale PD, Penkett SA |year=2001|title=Emissions of CH<sub>3</sub>Br, Organochlorines, and Organoiodines from Temperate Macroalgae|doi=10.1016/S1465-9972(00)00021-0|journal=Chemosphere - Global Change Science|volume=3|pages=93}}</ref> and ''Desmarestia antarctica'', ''Lambia antarctica'', ''Laminaria saccharina'', ''] ligulatum''.<ref>{{Cite journal|doi=10.1021/es049527s|pmid=15669318|year=2004|last1=Laturnus|first1=F|last2=Svensson|first2=T|last3=Wiencke|first3=C|last4=Oberg|first4=G|title=Ultraviolet radiation affects emission of ozone-depleting substances by marine macroalgae: results from a laboratory incubation study.|volume=38|issue=24|pages=6605–9|journal=Environmental science & technology}}</ref>
	==Production==		==Production==
			Industrially, chloroform is produced by heating a mixture of ] and either ] ({{chem2|CH3Cl}}) or ] ({{chem2|CH4}}).<ref name=Ullmann/> At 400–500&nbsp;°C, ] occurs, converting these precursors to progressively more chlorinated compounds:
	Chloroform was reported in 1831 by the French ] ], who prepared it from ] (2-propanone) as well as ] through the action of chlorine ] powder (]).<ref>{{Cite journal
			:{{chem2|CH4 + ] → CH3Cl + ]}}
	| author = ]
			:{{chem2|CH3Cl + Cl2 → ] + HCl}}
	| journal = Ann. Chim.
			:{{chem2|CH2Cl2 + Cl2 → CHCl3 + HCl}}
	| volume = 48
	| pages = 131
	| year = 1831}}</ref> The American physician ] prepared gallons of the material and described its "deliciousness of flavor."<ref>{{Cite journal
	| author = ]
	| title = New mode of preparing a spirituous solution of Chloric Ether
	| journal = Am. J. Sci. And Arts
	| volume = 21
	| pages = 64
	| year = 1832}}</ref> Independently, ] also described the same compound.<ref>{{Cite journal
	| author = ]
	| title = Ueber die Verbindungen, welche durch die Einwirkung des Chlors auf Alkohol, Aether, ölbildendes Gas und Essiggeist entstehen
	| journal = ]
	| volume = 1
	| issue = 2
	| pages = 182–230
	| year = 1832
	| doi = 10.1002/jlac.18320010203}}</ref> All early preparations used variations of the ]. Chloroform was named and chemically characterized in 1834 by ].<ref>{{Cite journal
	| author = ]
	| title = Untersuchung über die Wirkung des Chlors auf den Alkohol
	| journal = ]
	| volume = 107
	| issue = 41
	| pages = 650–656
	| year = 1834
	| doi = 10.1002/andp.18341074103}}</ref>
			Chloroform undergoes further chlorination to yield ] ({{chem2|CCl4}}):
	===Industrial routes===
			:{{chem2|CHCl3 + Cl2 → CCl4 + HCl}}
	In industry, chloroform is produced by heating a mixture of ] and either ] or ].<ref name=Ullmann/> At 400–500 °C, a ] occurs, converting these precursors to progressively more chlorinated compounds:
	:CH<sub>4</sub> + Cl<sub>2</sub> → CH<sub>3</sub>Cl + ]
	:CH<sub>3</sub>Cl + Cl<sub>2</sub> → ] + HCl
	:CH<sub>2</sub>Cl<sub>2</sub> + Cl<sub>2</sub> → CHCl<sub>3</sub> + HCl
			The output of this process is a mixture of the four chloromethanes: ], ] (dichloromethane), trichloromethane (chloroform), and tetrachloromethane (carbon tetrachloride). These can then be separated by ].<ref name=Ullmann/>
	Chloroform undergoes further chlorination to give ]:
	:CHCl<sub>3</sub> + Cl<sub>2</sub> → CCl<sub>4</sub> + HCl
			Chloroform may also be produced on a small scale via the ] between ] and ]:
	The output of this process is a mixture of the four chloromethanes, chloromethane, dichloromethane, chloroform, and carbon tetrachloride, which are then separated by ].<ref name=Ullmann/>
			:{{chem2|3 NaOCl + (CH3)2CO → CHCl3 + 2 ] + ]}}
	===Deuterochloroform===		===Deuterochloroform===
			{{Main|Deuterated chloroform}}
	An archaic industrial route to chloroform involved the reaction of acetone (or ethanol) with ] or calcium hypochlorite, the aforementioned ].<ref name=Ullmann/> The chloroform can be removed from the coproducts by distillation. A related reaction is still used in the production of ] and ]. Although the haloform process is obsolete for the production of ordinary chloroform, it is used to produce CDCl<sub>3</sub>.{{Citation needed|date=December 2007}} Deuterochloroform can also be prepared by the reaction of sodium deuteroxide with ],{{Citation needed|date=December 2007}} or from ordinary chloroform.<ref></ref>
			] is an ] of chloroform with a single ] atom. {{chem2|CDCl3}} is a common solvent used in ]. Deuterochloroform is produced by the reaction of ] with ].<ref>{{cite journal |last1=Paulsen |first1=P. J. |last2=Cooke |first2=W. D. |title=Preparation of Deuterated Solvents for Nuclear Magnetic Resonance Spectrometry. |journal=Analytical Chemistry |date=1 September 1963 |volume=35 |issue=10 |page=1560 |doi=10.1021/ac60203a072}}</ref> The haloform process is now obsolete for production of ordinary chloroform. Deuterochloroform can also be prepared by reacting ] with ].<ref>{{cite journal|doi=10.1021/ja01314a058|title=Chloroform-d (Deuteriochloroform)1|journal=Journal of the American Chemical Society|volume=57|issue=11|pages=2236–2237|year=1935|last1=Breuer|first1=F. W.}}</ref><ref>{{cite journal|doi=10.1021/jo01030a526|title=A Convenient Preparation of Chloroform-d1|journal=The Journal of Organic Chemistry|volume=29|issue=7|pages=2045–2046|year=1964|last1=Kluger|first1=Ronald}}</ref>
	===Inadvertent formation of chloroform===		===Inadvertent formation of chloroform===
	The haloform reaction can also occur inadvertently in domestic settings. Sodium hypochlorite solution (]) mixed with common household liquids such as ], ], ], or ] can produce some chloroform, in addition to other compounds such as ], or dichloroacetone.		The haloform reaction can also occur inadvertently in domestic settings. Sodium hypochlorite solution (]) mixed with common household liquids such as ], ], ], or ] can produce some chloroform, in addition to other compounds, such as ] or ].{{citation needed|date=November 2020}}
	==Uses==		==Uses==
			In terms of scale, the most important reaction of chloroform is with ] to give ] (HCFC-22), a precursor in the production of polytetrafluoroethylene (]) and other fluoropolymers:<ref name="Ullmann" />
	The major use of chloroform today is in the production of the ] (R-22), a major precursor to ]:
	:CHCl<sub>3</sub> + 2 HF → CHClF<sub>2</sub> + 2 HCl		:{{chem2|CHCl3 + 2 HF → CHClF2 + 2 HCl}}
	The reaction is conducted in the presence of a catalytic amount of ]. Chlorodifluoromethane is then converted into tetrafluoroethylene, the main precursor to ]. Before the ], chlorodifluoromethane (R22) was also a popular refrigerant.		The reaction is conducted in the presence of a ] amount of ]. Chlorodifluoromethane is then converted to ], the main precursor of ].<ref>{{Cite web|title=Chlorodifluoromethane {{!}} chemical compound|url=https://www.britannica.com/science/chlorodifluoromethane|access-date=2021-09-08|website=Encyclopedia Britannica|language=en|archive-date=17 July 2021|archive-url=https://web.archive.org/web/20210717174046/https://www.britannica.com/science/chlorodifluoromethane|url-status=live}}</ref>
	====As a solvent====		===Solvent===
			The ] attached to ] in chloroform participates in hydrogen bonding,<ref>{{cite journal|last1=Wiley |first1=G. R. |last2=Miller |first2=S. I. |doi=10.1021/ja00765a001|title=Thermodynamic parameters for hydrogen bonding of chloroform with Lewis bases in cyclohexane. Proton magnetic resonance study|year=1972|journal=Journal of the American Chemical Society|volume=94|issue=10|pages=3287–3293}}</ref><ref>{{cite journal|pmid=18855462|year=2008|last1=Kwak|first1=K.|last2=Rosenfeld|first2=D. E.|last3=Chung|first3=J. K.|last4=Fayer|first4=M. D.|title=Solute-solvent complex switching dynamics of chloroform between acetone and dimethylsulfoxide-two-dimensional IR chemical exchange spectroscopy|volume=112|issue=44|pages=13906–13915|doi=10.1021/jp806035w|pmc=2646412|journal=The Journal of Physical Chemistry B}}</ref> making it a good solvent for many materials.
	Chloroform is a common solvent in the laboratory because it is relatively unreactive, miscible with most organic liquids, and conveniently volatile. Chloroform is used as a ] in the ] industry and for producing ]s and ]s. Chloroform is an effective solvent for ]s in their base form and thus plant material is commonly extracted with chloroform for pharmaceutical processing. For example, it is used in commerce to extract ] from ] and ] from '']'' plants. Chloroform containing ] (heavy hydrogen), ], is a common solvent used in ]. It can be used to bond pieces of ] (also known under the trade names Perspex and Plexiglas). A solvent of phenol:chloroform:isoamyl alcohol 25:24:1 is used to dissolve non-nucleic acid biomolecules in DNA and RNA extractions.
			Worldwide, chloroform is also used in pesticide formulations, as a ] for ], ], ]s, ]es, ], and ]s, as a cleaning agent, as a grain ], in ], and in the rubber industry.<ref name="cicad">{{citation | title=Chloroform | series=] | volume=58 | publisher=] | year=2004 | url=https://www.who.int/ipcs/publications/cicad/en/cicad58.pdf | url-status=live | archive-url=https://web.archive.org/web/20200731202031/https://www.who.int/ipcs/publications/cicad/en/cicad58.pdf | archive-date=31 July 2020}}</ref><ref name="pth">{{cite encyclopedia| editor1-last=Leikin |editor1-first=Jerrold B. | editor2-last=Paloucek |editor2-first=Frank P. | title=Chloroform | encyclopedia=Poisoning and Toxicology Handbook | edition=4th | publisher=Informa | year=2008 | page=774}}</ref> ] is a common solvent used in ].<ref>{{cite journal|doi=10.1021/om100106e|title=NMR Chemical Shifts of Trace Impurities: Common Laboratory Solvents, Organics, and Gases in Deuterated Solvents Relevant to the Organometallic Chemist|journal=Organometallics|volume=29|issue=9|pages=2176–2179|year=2010|last1=Fulmer|first1=Gregory R.|last2=Miller|first2=Alexander J. M.|last3=Sherden|first3=Nathaniel H.|last4=Gottlieb|first4=Hugo E.|last5=Nudelman|first5=Abraham|last6=Stoltz|first6=Brian M.|last7=Bercaw|first7=John E.|last8=Goldberg|first8=Karen I.|s2cid=2755004 |url=https://authors.library.caltech.edu/18475/2/om100106e_si_001.pdf}}</ref>
	====As a reagent in organic synthesis====
	As a ], chloroform serves as a source of the dichlorocarbene CCl<sub>2</sub> group.<ref>Srebnik, M.; Laloë, E. "Chloroform" Encyclopedia of Reagents for Organic Synthesis" 2001 John Wiley.{{doi|10.1002/047084289X.rc105}}</ref> It reacts with aqueous ] usually in the presence of a ] to produce ], CCl<sub>2</sub>.<ref>{{OrgSynth|Vogel, E.; Klug, W.; Breuer. A.|title = <nowiki>1,6-Methanoannulene</nowiki>|collvol = 6|collvolpages = 731|year = 1988|prep = cv6p0731}}</ref><ref>{{OrgSynth|author = Gokel, G. W.; Widera, R. P.; Weber, W. P.|title = Phase-Transfer Hofmann Carbylamine Reaction: tert-Butyl Isocyanide|collvol = 6|collvolpages = 232|year = 1988|prep = cv6p0232}}</ref> This reagent affects ortho-formylation of activated ] such as ], producing aryl ]s in a reaction known as the ]. Alternatively the ] can be trapped by an ] to form a ] derivative. In the ] chloroform forms the CHCl<sub>2</sub> free radical in addition to alkenes.
	====As an anesthetic====		===Refrigerant===
			Chloroform is used as a precursor to make R-22 (chlorodifluoromethane). This is done by reacting it with a solution of ] (HF) which fluorinates the {{chem2|CHCl3}} molecule and releases hydrochloric acid as a byproduct.<ref>{{cite web | url=https://www.ebi.ac.uk/chebi/es/searchId.do?printerFriendlyView=true&locale=null&chebiId=35255&viewTermLineage=null&structureView=&|title=Chloroform (CHEBI:35255)}}</ref> Before the ] was enforced, most of the chloroform produced in the United States was used in the production of ]. However, its production remains high, as it is a key precursor of PTFE.<ref>{{cite web|url=https://www.atsdr.cdc.gov/ToxProfiles/tp6-c4.pdf|title=Production, import/export, use, and disposal|access-date=5 April 2023|website=atsdr.cdc.gov}}</ref>
			Although chloroform has properties such as a low boiling point, and a low global warming potential of only 31 (compared to the 1760 of R-22), which are appealing properties for a refrigerant, there is little information to suggest that it has seen widespread use as a refrigerant in any consumer products.<ref>{{cite encyclopedia| title=Chloroform as a pollutant |encyclopedia=The Encyclopedia of World Problems | url=http://encyclopedia.uia.org/en/problem/chloroform-pollutant#:~:text=Most%20chloroform%20is%20manufactured%20to,spot%20removers%2C%20and%20various%20solvents}}</ref>
	]
			===Lewis acid===
	Chloroform was once a popular ]; its vapor depresses the ] of a patient, allowing a doctor to perform various otherwise painful procedures. In 1847, the Scottish ] ] first used chloroform for ] during ]. The use of chloroform during ] expanded rapidly thereafter in Europe. In the United States, chloroform began to replace ] as an anesthetic at the beginning of the 20th century; however, it was quickly abandoned in favor of ether upon discovery of its toxicity, especially its tendency to cause fatal ] analogous to what is now termed "]". ] is still the preferred anesthetic in some ]s due to its high ] (~1.5–2.2) <ref>{{Cite journal|author=Calderone, F.A. |journal=J. Pharmacology Experimental Therapeutics|year=1935|volume=55|pages=24|url=http://jpet.aspetjournals.org/cgi/reprint/55/1/24.pdf}}</ref> and low price. One possible mechanism of action for chloroform is that it increases movement of potassium ions through certain types of ] in ].<ref>{{Cite journal|last1 = Patel|first1 = Amanda J.|last2 = Honoré|first2 = Eric|last3 = Lesage|first3 = Florian|last4 = Fink|first4 = Michel|last5 = Romey|first5 = Georges|last6 = Lazdunski|first6 = Michel|publication-date =|date = May 1999|title = Inhalational anesthetics activate two-pore-domain background K+ channels|journal = Nature Neuroscience|volume = 2|pages = 422–426|doi = 10.1038/8084|pmid = 10321245|issue = 5|author2 = Honoré|author3 = Lesage|author4 = Fink|author5 = Romey|author6 = Lazdunski}}</ref> Chloroform could also be mixed with other anaesthetic agents such as ] to make C.E. mixture, or ether and ] to make ].
			In solvents such as {{chem2|CCl4}} and alkanes, chloroform hydrogen bonds to a variety of Lewis bases. {{chem2|HCCl3}} is classified as a ], and the ] lists its acid parameters as E<sub>A</sub> = 1.56 and C<sub>A</sub> = 0.44.
	====Veterinary use====		===Reagent===
			As a ], chloroform serves as a source of the ] intermediate {{chem2|CCl2}}.<ref>{{cite encyclopedia|last1=Srebnik |first1=M. |last2=Laloë |first2=E. |date=2001 |encyclopedia=Encyclopedia of Reagents for Organic Synthesis |publisher=Wiley |doi=10.1002/047084289X.rc105|chapter=Chloroform |isbn=978-0-471-93623-7 }}</ref> It reacts with aqueous ], usually in the presence of a ], to produce ], {{chem2|CCl2}}.<ref>{{OrgSynth|last1=Vogel |first1=E. |last2=Klug |first2=W. |last3=Breuer |first3=A.|title = 1,6-Methanoannulene|collvol = 6|collvolpages = 731|year = 1988|prep = cv6p0731}}</ref><ref>{{OrgSynth|last1 = Gokel |first1=G. W. |last2=Widera|first2= R. P. |last3=Weber |first3=W. P.|title = Phase-Transfer Hofmann Carbylamine Reaction: ''tert''-Butyl Isocyanide|collvol = 6|collvolpages = 232|year = 1988|prep = cv6p0232}}</ref> This reagent effects ortho-formylation of activated ], such as ], producing aryl ]s in a reaction known as the ]. Alternatively, the ] can be trapped by an ] to form a ] derivative. In the ], chloroform forms the {{chem2|•CHCl2}} free radical which adds to alkenes.{{citation needed|date=November 2020}}
	In veterinary medicine it is used externally to kill maggots in wounds.{{Citation needed|date=November 2010}}
			===Anaesthetic===
			]
			Chloroform is a powerful ], ], ], and ] when inhaled or ingested. The ] qualities of chloroform were first described in 1842 in a thesis by ], which won the Gold Medal of the ] for that year.<ref>{{cite journal |last1=Perkins-McVey |first1=Matthew |title="A new order of poisonous substances": revisiting Robert M. Glover's dissertation on the physiological effects of bromine, chlorine, and iodine compounds |journal=Naunyn-Schmiedeberg's Archives of Pharmacology |date=10 November 2023 |volume=397 |issue=5 |pages=3343–3350 |doi=10.1007/s00210-023-02820-y |url=https://www.researchgate.net/publication/375556103 |access-date=27 January 2024|doi-access=free |pmid=37947840 }}</ref><ref>{{cite journal |last1=Glover |first1=Robert M. |title=On the Physiological and Medicinal Properties of Bromine and Its Compounds; Also on the Analogies between the Physiological and Medicinal Properties of These Bodies, and Those of Chlorine and Iodine, with Their Correspondent Compounds; Being the Harveian Prize Essay for 1842. |journal=Edinburgh Medical and Surgical Journal |date=1 October 1842 |volume=58 |issue=153 |pages=335–364 |pmid=30330609 |pmc=5789197 }}</ref> Glover also undertook practical experiments on dogs to prove his theories, refined his theories, and presented them in his doctoral thesis at the ] in the summer of 1847, identifying anaesthetizing halogenous compounds as a "new order of poisonous substances".<ref>{{cite journal |last1=Perkins-McVey |first1=Matthew |title="A new order of poisonous substances": revisiting Robert M. Glover's dissertation on the physiological effects of bromine, chlorine, and iodine compounds |journal=Naunyn-Schmiedeberg's Archives of Pharmacology |date=10 November 2023 |volume=397 |issue=5 |pages=3343–3350 |doi=10.1007/s00210-023-02820-y |url=https://www.researchgate.net/publication/375556103 |access-date=27 January 2024|doi-access=free |pmid=37947840 }}</ref>
			The Scottish ] ] was one of those examiners required to read the thesis, but later claimed to have never read it and to have come to his own conclusions independently. <ref>{{cite journal |last1=Perkins-McVey |first1=Matthew |title="A new order of poisonous substances": revisiting Robert M. Glover's dissertation on the physiological effects of bromine, chlorine, and iodine compounds |journal=Naunyn-Schmiedeberg's Archives of Pharmacology |date=10 November 2023 |volume=397 |issue=5 |pages=3343–3350 |doi=10.1007/s00210-023-02820-y |url=https://www.researchgate.net/publication/375556103 |access-date=27 January 2024|doi-access=free |pmid=37947840 }}</ref> Perkins-McVey, among others, have raised doubts about the credibility of Simpson's claim, noting that Simpson's publications on the subject in 1847 explicitly echo Glover's and, being one of the thesis examiners, Simpson was likely aware of the content of Glover's study, even if he skirted his duties as an examiner. <ref>{{cite journal |last1=Perkins-McVey |first1=Matthew |title="A new order of poisonous substances": revisiting Robert M. Glover's dissertation on the physiological effects of bromine, chlorine, and iodine compounds |journal=Naunyn-Schmiedeberg's Archives of Pharmacology |date=10 November 2023 |volume=397 |issue=5 |pages=3343–3350 |doi=10.1007/s00210-023-02820-y |url=https://www.researchgate.net/publication/375556103 |access-date=27 January 2024|doi-access=free |pmid=37947840 }}</ref> In 1847 and 1848, Glover would pen a series of heated letters accusing Simpson of stealing his discovery, which had already earned Simpson considerable notoriety. <ref>{{cite journal |last1=Perkins-McVey |first1=Matthew |title="A new order of poisonous substances": revisiting Robert M. Glover's dissertation on the physiological effects of bromine, chlorine, and iodine compounds |journal=Naunyn-Schmiedeberg's Archives of Pharmacology |date=10 November 2023 |volume=397 |issue=5 |pages=3343–3350 |doi=10.1007/s00210-023-02820-y |url=https://www.researchgate.net/publication/375556103 |access-date=27 January 2024|doi-access=free |pmid=37947840 }}</ref> Whatever the source of his inspiration, on 4 November 1847, Simpson argued that he had discovered the anaesthetic qualities of chloroform in humans. He and two colleagues entertained themselves by trying the effects of various substances, and thus revealed the potential for chloroform in medical procedures.<ref name="Gordon2002">{{cite book|last=Gordon|first=H. Laing|title=Sir James Young Simpson and Chloroform (1811–1870)|url=https://books.google.com/books?id=pYer05UwKBYC&pg=PA106|date=November 2002|publisher=Minerva Group|isbn=978-1-4102-0291-8|pages=106–109|access-date=5 January 2016|archive-date=6 May 2016|archive-url=https://web.archive.org/web/20160506214333/https://books.google.com/books?id=pYer05UwKBYC&pg=PA106|url-status=live}}</ref>
			]
			A few days later, during the course of a dental procedure in ], ] became the first person to use chloroform on a patient in a clinical context.<ref>{{cite web |last=Dingwall |date=April 2004 |url=http://historyofdentistry.co.uk/index_htm_files/2004Apr2.pdf |title=A pioneering history: dentistry and the Royal College of Surgeons of Edinburgh |website=historyofdentistry.co.uk |archive-url=https://web.archive.org/web/20130201191323/http://historyofdentistry.co.uk/index_htm_files/2004Apr2.pdf |archive-date=1 February 2013}}</ref>
			In May 1848, ] made a presentation to the Medico-Chirurgical Society of Edinburgh following a series of laboratory ] that confirmed Glover's findings and also refuted Simpson's claims of originality. The laboratory experiments that proved the dangers of chloroform were largely ignored.<ref>{{cite journal |url=https://www.royalsoced.org.uk/cms/files/research_awards/prizes/prize_lists/gunning_victoria_history.pdf |title=Robert Halliday Gunning and the Victoria Jubilee Prizes |year=2003 |access-date=2016-08-18 |archive-url=https://web.archive.org/web/20160822105053/https://www.royalsoced.org.uk/cms/files/research_awards/prizes/prize_lists/gunning_victoria_history.pdf |archive-date=22 August 2016 |doi=10.1177/003693300304800209 |last1=Baillie |first1=T. W. |journal=Scottish Medical Journal |volume=48 |issue=2 |pages=54–57 |pmid=12774598 |s2cid=10998512 }}</ref>
			The use of chloroform during ] expanded rapidly in Europe; for instance in the 1850s chloroform was used by the physician ] during the births of ]'s last two children ] and ].<ref>{{cite web |url=http://www.ph.ucla.edu/epi/snow/victoria.html |title=Anesthesia and Queen Victoria |website=ph.ucla.edu |access-date=13 August 2012 |url-status=live |archive-url=https://web.archive.org/web/20120716005223/http://www.ph.ucla.edu/epi/snow/victoria.html |archive-date=16 July 2012}}</ref> In the United States, chloroform began to replace ] as an anesthetic at the beginning of the 20th century;{{cn|date=February 2023}} it was abandoned in favor of ether on discovery of its toxicity, especially its tendency to cause fatal ] analogous to what is now termed "]". Some people used chloroform as a recreational drug or to attempt suicide.<ref>{{cite journal|last=Martin|first=William|title=A Case of Chloroform Poisoning; Recovery|journal=British Medical Journal|date=3 July 1886|volume=2|issue=1331|pages=16–17|pmc=2257365|doi=10.1136/bmj.2.1331.16-a|pmid=20751619}}</ref> One possible mechanism of action of chloroform is that it increases the movement of ] ions through certain types of ]s in ].<ref>{{Cite journal|last1 = Patel|first1 = Amanda J.|last2 = Honoré|first2 = Eric|last3 = Lesage|first3 = Florian|last4 = Fink|first4 = Michel|last5 = Romey|first5 = Georges|last6 = Lazdunski|first6 = Michel|date = May 1999|title = Inhalational anesthetics activate two-pore-domain background K<sup>+</sup> channels|journal = Nature Neuroscience|volume = 2|pages = 422–426|doi = 10.1038/8084|pmid = 10321245|issue = 5|s2cid = 23092576}}</ref> Chloroform could also be mixed with other anaesthetic agents such as ether to make C.E. mixture, or ether and ] to make ].{{citation needed|date=November 2020}}
			In 1848, Hannah Greener, a 15-year-old girl who was having an infected toenail removed, died after being given the anaesthetic.<ref>{{cite journal|title=An Unexplained Death: Hannah Greener and Chloroform |last1=Knight |first1=Paul R. III |last2=Bacon |first2=Douglas R. |s2cid=12865865 | year=2002 |volume = 96 |issue = 5 |journal=Anesthesiology|doi=10.1097/00000542-200205000-00030|pages=1250–1253|pmid=11981167|doi-access=free }}</ref> Her autopsy establishing the cause of death was undertaken by ] assisted by ].<ref name=pdf1/> A number of physically fit patients died after inhaling it. In 1848, however, John Snow developed an inhaler that regulated the dosage and so successfully reduced the number of deaths.<ref>{{cite book|last1 = Snow|first1 = John|year = 1858|title = On Chloroform and Other Anaesthetics and Their Action and Administration|pages = 82–85|url = https://archive.org/stream/onchloroformothe1858snow#page/82/mode/2up/search/inhaler|url-status = live|archive-url = http://archive.wikiwix.com/cache/20151123021418/https://archive.org/stream/onchloroformothe1858snow#page/82/mode/2up/search/inhaler|archive-date = 23 November 2015|publisher = London : John Churchill}}</ref>
			The opponents and supporters of chloroform disagreed on the question of whether the medical complications were due to respiratory disturbance or whether chloroform had a specific effect on the heart. Between 1864 and 1910, numerous commissions in Britain studied chloroform but failed to come to any clear conclusions. It was only in 1911 that Levy proved in experiments with animals that chloroform can cause ventricular fibrillation.{{Citation needed|date=March 2023}} Despite this, between 1865 and 1920, chloroform was used in 80 to 95% of all narcoses performed in the UK and German-speaking countries. In Germany, comprehensive surveys of the fatality rate during anaesthesia were made by Gurlt between 1890 and 1897.{{Citation needed|date=March 2023}} At the same time in the UK the medical journal '']'' carried out a questionnaire survey<ref>{{Cite journal |last=Anonymous. |date=1890 |title=The Lancet Inquiry into the Mortality Under Anaesthetics. |journal=Lancet |volume=145 |issue=3472 |pages=612–13}}</ref> and compiled a report detailing numerous adverse reactions to anesthetics, including chloroform.<ref>{{Cite journal |last=Anonymous. |date=1893 |title=Report of The Lancet Commission appointed to investigate the subject of the administration of chloroform and other anesthetics from a clinical standpoint. |journal=Lancet |volume=141 |issue=3629 |pages=629–38}}</ref> In 1934, Killian gathered all the statistics compiled until then and found that the chances of suffering fatal complications under ether were between 1:14,000 and 1:28,000, whereas with chloroform the chances were between 1:3,000 and 1:6,000.{{Citation needed|date=March 2023}} The rise of gas anaesthesia using ], improved equipment for administering anesthetics, and the discovery of ] in 1932 led to the gradual decline of chloroform narcosis.<ref>{{cite journal | pmid = 9487785 | volume=22 | issue=6 | title=History of chloroform anesthesia | year=1997 | journal=Anesthesiology and Reanimation | pages=144–152 | last= Wawersik |first=J.}}</ref>
			The latest reported anaesthetic use of chloroform in the Western world dates to 1987, when the last doctor who used it retired, about 140 years after its first use.<ref>{{cite book|last=Stratmann|first=Linda|date=2003|title=Chloroform: The Quest for Oblivion|location=Stroud|publisher=Sutton Publishing|isbn=978-0-7524-9931-4}}</ref>
			=== Criminal use ===
			Chloroform has been used by criminals to knock out, daze, or murder victims. Joseph Harris was charged in 1894 with using chloroform to rob people.<ref>{{cite news|url=https://news.google.com/newspapers?id=Ec1VAAAAIBAJ&pg=2904,2720400&dq=chloroform+knockout&hl=en|title=Knock-out and Chloroform|newspaper=]|date=9 February 1894|access-date=31 March 2011|archive-date=20 January 2022|archive-url=https://web.archive.org/web/20220120054325/https://news.google.com/newspapers?id=Ec1VAAAAIBAJ&pg=2904,2720400&dq=chloroform+knockout&hl=en|url-status=live}}</ref> ] ] used chloroform overdoses to kill his female victims. In September 1900, chloroform was implicated in the murder of the U.S. businessman ]. Chloroform was deemed a factor in the alleged murder of a woman in 1991, when she was asphyxiated while asleep.<ref>{{cite news|url=https://news.google.com/newspapers?id=I91HAAAAIBAJ&pg=2367,1007950&dq=chloroform+knockout&hl=en|title=Chloroform case retrial underway|date=7 July 1993|access-date=31 March 2011|newspaper=]|archive-date=6 November 2021|archive-url=https://web.archive.org/web/20211106203133/https://news.google.com/newspapers?id=I91HAAAAIBAJ&pg=2367%2C1007950&dq=chloroform+knockout&hl=en|url-status=live}}</ref> In 2002, 13-year-old ] was sedated with chloroform when she was abducted by David Fuller and during the time that he had her, before he shot and killed her.<ref>{{Cite web|url=https://www.arkansasonline.com/news/2003/dec/17/not-forgotten/|title=But not forgotten|last=Cathy Frye - ]|date=2003-12-17|website=www.arkansasonline.com|access-date=2021-12-07|archive-date=7 December 2021|archive-url=https://web.archive.org/web/20211207200713/https://www.arkansasonline.com/news/2003/dec/17/not-forgotten/|url-status=live}}</ref> In a 2007 plea bargain, a man confessed to using ] and chloroform to sexually assault minors.<ref>{{cite news|url=https://www.usatoday.com/news/nation/2007-11-06-chloroform-rapes_N.htm|title=Man admits to raping friends' daughters|date=6 November 2007|access-date=31 March 2011|newspaper=]|url-status=live|archive-url=https://web.archive.org/web/20110429075437/http://www.usatoday.com/news/nation/2007-11-06-chloroform-rapes_N.htm|archive-date=29 April 2011}}</ref>
			The use of chloroform as an ] has become widely recognized, bordering on ], through the adoption by ] authors of plots involving criminals' use of chloroform-soaked rags to render victims unconscious. However, it is nearly impossible to incapacitate someone using chloroform in this way.<ref name="Anaesthesia">{{cite journal|last=Payne|first=J. P.|s2cid=1718276|date=July 1998|title=The criminal use of chloroform|journal=]|volume=53|issue=7|pages=685–690|doi=10.1046/j.1365-2044.1998.528-az0572.x|pmid=9771177|doi-access=free}}</ref> It takes at least five minutes of inhalation of chloroform to render a person unconscious. Most criminal cases involving chloroform involve co-administration of another drug, such as ] or ], or the victim being complicit in its administration. After a person has lost consciousness owing to chloroform inhalation, a continuous volume must be administered, and the chin must be supported to keep the tongue from obstructing the airway, a difficult procedure, typically requiring the skills of an ]. In 1865, as a direct result of the criminal reputation chloroform had gained, the medical journal '']'' offered a "permanent scientific reputation" to anyone who could demonstrate "instantaneous insensibility", i.e. loss of consciousness, using chloroform.<ref>{{cite journal|title=Medical Annotation: Chloroform amongst Thieves |journal=] |date=1865 |volume=2 |issue=2200 |pages=490–491|doi=10.1016/s0140-6736(02)58434-8}}</ref>
	==Safety==		==Safety==
			===Exposure===
	Fatal oral dose of chloroform may be as low as 10 mL (14.8 g), with death due to respiratory or cardiac arrest.<ref>, US Environmental Potection Agency</ref>
			Chloroform is formed as a by-product of ], along with a range of other ]s, and it is therefore often present in municipal tap water and swimming pools. Reported ranges vary considerably, but are generally below the current health standard for total ] (THMs) of 100 μg/L.<ref>{{cite journal|last1=Nieuwenhuijsen|first1=MJ|last2=Toledano|first2=MB|last3=Elliott|first3=P|title=Uptake of chlorination disinfection by-products; a review and a discussion of its implications for exposure assessment in epidemiological studies.|journal=Journal of Exposure Analysis and Environmental Epidemiology|date=8 August 2000|volume=10|issue=6 Pt 1|pages=586–99|pmid=11140442|doi=10.1038/sj.jea.7500139|doi-access=free}}</ref> However, when considered in combination with other trihalomethanes often present in drinking water, the concentration of THMs often exceeds the recommended limit of exposure.<ref>{{Cite web |title=EWG's Tap Water Database: Contaminants in Your Water |url=https://www.ewg.org/tapwater/reviewed-disinfection-byproducts.php |access-date=2023-08-08 |website=www.ewg.org |language=en}}</ref>
			While few studies have assessed the risks posed by chloroform exposure through drinking water in isolation from other THMs, many studies have shown that exposure to the general category of THMs, including chloroform, is associated with an increased risk of cancer of the bladder or lower GI tract.<ref>{{Cite web |title=Public Health Goals for Trihalomethanes in Drinking Water |page=93 |url=https://oehha.ca.gov/media/downloads/water/chemicals/phg/thmsphg020720.pdf |access-date=2023-08-08 |website=oehha.ca.gov}}</ref>
	As might be expected for an ], chloroform vapors depress the ]. It is ] at approximately 500 ], according to the ]. Breathing about 900 ppm for a short time can cause dizziness, fatigue, and headache. Chronic chloroform exposure can damage the ] (where chloroform is metabolized to ]) and to the ]s, and some people develop sores when the skin is immersed in chloroform.
			Historically, chloroform exposure may well have been higher, owing to its common use as an anesthetic, as an ingredient in cough syrups, and as a constituent of ], where ] had previously been used as a ].<ref>Yin-Tak Woo, David Y. Lai, Joseph C. Arcos {{webarchive|url=https://web.archive.org/web/20180605033237/https://books.google.com/books?id=25H-BAAAQBAJ&pg=PA98&lpg=PA98&dq=Chloroform+tobacco&source=bl&ots=GGoHCH5uup&sig=vJAm_Ecl4J_XuHn5EXIZ9Jpik4E&hl=en&sa=X&ved=0ahUKEwjPrLX9hbvUAhXDDsAKHeIOC3gQ6AEILzAC |date=5 June 2018 }}</ref>
	] have shown that ]s occur in ]s and ] that have breathed ] containing 30 to 300 ] of chloroform during ] and also in rats that have ingested chloroform during pregnancy. ] of rats and mice that breathed chloroform during pregnancy have a higher incidence of ]s, and abnormal ] have been found in male mice that have breathed air containing 400 ppm chloroform for a few days. The effect of chloroform on ] in humans is unknown.
			===Pharmacology===
	Chloroform once appeared in ]s, ]s, ]s, and other ]s, but it has been banned as a ] in the US since 1976.<ref>{{Cite web| title= The National Toxicology Program: Substance Profiles: Chloroform CAS No. 67-66-3| url=http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s038chlo.pdf| format=pdf| accessdate=2007-11-02}}</ref> Cough syrups containing Chloroform can still be legally purchased in pharmacies and supermarkets in the UK.
			Chloroform is well absorbed, metabolized, and eliminated rapidly by mammals after oral, inhalation, or dermal exposure. Accidental splashing into the eyes has caused irritation.<ref name="cicad" /> Prolonged dermal exposure can result in the development of sores as a result of ]. Elimination is primarily through the lungs as chloroform and carbon dioxide; less than 1% is excreted in the urine.<ref name="pth" />
			Chloroform is metabolized in the liver by the ] enzymes, by oxidation to trichloromethanol and by reduction to the dichloromethyl ]. Other metabolites of chloroform include ] and diglutathionyl dithiocarbonate, with ] as the predominant end-product of metabolism.<ref name="eot">{{cite encyclopedia| first=Anna M. |last=Fan | title=Chloroform | encyclopedia=Encyclopedia of Toxicology | edition=2nd | volume=1 | publisher=Elsevier | year=2005 | pages=561–565}}</ref>
	The US National Toxicology Program's eleventh report on carcinogens<ref>{{Cite web| title= 11th Report on Carcinogens| url=http://ntp.niehs.nih.gov/ntp/roc/toc11.html| accessdate=2007-11-02}}</ref> implicates it as reasonably anticipated to be a human ], a designation equivalent to ] class 2A. The IARC itself classifies chloroform as ''possibly carcinogenic to humans'', a Group 2B designation.<ref>{{Cite web| title= International Agency for Research on Cancer (IARC) - Summaries & Evaluations: Chloroform| url=http://www.inchem.org/documents/iarc/vol73/73-05.html| accessdate=2010-09-02}}</ref> It has been most readily associated with ].<ref>{{Cite web| url=http://www.cdc.gov/Niosh/78127_9.html| title=Centers for Disease Control and Prevention: Current Intelligence Bulletin 9}}</ref><ref>{{Cite web| title= National Toxicology Program: Report on the carcinogenesis bioassay of chloroform|url=http://ntp.niehs.nih.gov/ntp/htdocs/LT_rpts/trChloroform.pdf}}</ref> Caution is mandated during its handling in order to minimize unnecessary exposure; safer alternatives, such as ], have resulted in a substantial reduction of its use as a solvent.
			Like most other general anesthetics and sedative-hypnotic drugs, chloroform is a ] at ].<ref>{{Cite journal|last1=Jenkins|first1=Andrew|last2=Greenblatt|first2=Eric P.|last3=Faulkner|first3=Howard J.|last4=Bertaccini|first4=Edward|last5=Light|first5=Adam|last6=Lin|first6=Audrey|last7=Andreasen|first7=Alyson|last8=Viner|first8=Anna|last9=Trudell|first9=James R.|last10=Harrison|first10=Neil L.|date=2001-03-15|title=Evidence for a Common Binding Cavity for Three General Anesthetics within the GABAA Receptor|journal=Journal of Neuroscience|language=en|volume=21|issue=6|pages=RC136|doi=10.1523/JNEUROSCI.21-06-j0002.2001|issn=0270-6474|pmid=11245705|pmc=6762625|doi-access=free}}</ref> Chloroform causes depression of the ] (CNS), ultimately producing deep ] and respiratory center depression.<ref name="eot" /> When ingested, chloroform causes symptoms similar to those seen after inhalation. Serious illness has followed ingestion of {{convert|7.5|g|oz|abbr=on}}. The mean lethal oral dose in an adult is estimated at {{convert|45|g|oz|abbr=on}}.<ref name="cicad" />
			The anesthetic use of chloroform has been discontinued, because it caused deaths from respiratory failure and cardiac arrhythmias. Following chloroform-induced anesthesia, some patients suffered ], ], ], ], and coma owing to ]. At autopsy, liver ] and degeneration have been observed.<ref name="cicad" /> The hepatotoxicity and nephrotoxicity of chloroform is thought to be due largely to ], one of its metabolites.<ref name="eot" />
	===Conversion to phosgene===		===Conversion to phosgene===
			Chloroform converts slowly in the presence of UV light and air to the extremely poisonous gas, ] ({{chem2|COCl2}}), releasing ] in the process.<ref name="earlham">{{cite web|url=http://www.earlham.edu/chemical-hygiene-and-safety/safety-topics/chloroform-and-phosgene/|title=Chloroform and Phosgene, Chemical Hygiene and Safety|website=Earlham College|access-date=17 August 2017|url-status=live|archive-url=https://web.archive.org/web/20170819102644/http://www.earlham.edu/chemical-hygiene-and-safety/safety-topics/chloroform-and-phosgene/|archive-date=19 August 2017}}</ref>
	During prolonged storage in the presence of ] chloroform converts slowly to ]. To prevent accidents, commercial chloroform is stabilized with ] or ], but samples that have been recovered or dried no longer contain any stabilizer. Amylene has been found ineffective, and the phosgene can affect analytes in samples, lipids and nucleic acids dissolved in or extracted with chloroform.<ref>(Turk, Eric, "Phosgene from Chloroform", Chemical & Engineering News (2 March 1998) Vol. 76, No. 9, pp.&nbsp;6.)</ref> Dissolved phosgene cannot be removed by distillation or carbon filters, but is removed by calcium hydroxide or activated alumina.<ref>(Cone, Edward J., William F. Buckwald, and William D. Darwin, "Analytical controls in Drug Metabolic Studies, II Artifact formation During Chloroform Extraction of Drugs and Metabolites with Amine Substituents",Drug Metabolism & Disposition November 1982 vol. 10 no. 6 561-567)</ref>
	Suspicious samples can be tested for phosgene using filter paper (treated with 5% diphenylamine, 5% dimethylaminobenzaldehyde in alcohol, and then dried), which turns yellow in phosgene vapor. There are several colorimetric and fluorometric reagents for phosgene, and it can also be quantified with mass spectrometry.
			:{{chem2|2 CHCl3 + O2 → 2 COCl2 + 2 HCl}}
	==References==
			To prevent accidents, commercial chloroform is stabilized with ] or ], but samples that have been recovered or dried no longer contain any stabilizer. Amylene has been found to be ineffective, and the phosgene can affect analytes in samples, lipids, and nucleic acids dissolved in or extracted with chloroform.<ref>{{cite journal|url=http://pubs.acs.org/cen/safety/19980302.html|last=Turk|first=Eric|title=Phosgene from Chloroform|journal=Chemical & Engineering News|date=2 March 1998|volume=76|issue=9|page=6|doi=10.1021/cen-v076n009.p006|doi-access=free|access-date=13 August 2012|archive-date=24 July 2008|archive-url=https://web.archive.org/web/20080724065839/http://pubs.acs.org/cen/safety/19980302.html|url-status=live}}</ref> When ethanol is used as a stabiliser for chloroform, it reacts with phosgene (which is soluble in chloroform) to form the relatively harmless ] ester:
	{{Reflist|2}}
			:2 CH<sub>3</sub>CH<sub>2</sub>OH + COCl<sub>2</sub> → CO<sub>3</sub>(CH<sub>2</sub>CH<sub>3</sub>)<sub>2</sub> + 2 HCl
			Phosgene and HCl can be removed from chloroform by washing with saturated aqueous ] solutions, such as ]. This procedure is simple and results in harmless products. Phosgene reacts with water to form ] and HCl,<ref>{{cite web |url=https://www.britannica.com/EBchecked/topic/457363/phosgene |title=phosgene (chemical compound) |website=Encyclopædia Britannica |access-date=16 August 2013 |url-status=live |archive-url=https://web.archive.org/web/20130605183448/https://www.britannica.com/EBchecked/topic/457363/phosgene |archive-date=5 June 2013}}</ref> and the carbonate salt ] the resulting acid.<ref>{{Cite journal |last1=Manogue |first1=W. H. |last2=Pigford |first2=R. L. |date=September 1960 |title=The kinetics of the absorption of phosgene into water and aqueous solutions |url=https://onlinelibrary.wiley.com/doi/10.1002/aic.690060329 |journal=AIChE Journal |language=en |volume=6 |issue=3 |pages=494–500 |doi=10.1002/aic.690060329 |bibcode=1960AIChE...6..494M |issn=0001-1541}}</ref>
			Suspected samples can be tested for phosgene using filter paper which when treated with 5% ], 5% ] in ], and then dried, turns yellow in the presence of phosgene vapour.<ref>{{Cite web |title=American Chemical Society: Chemical & Engineering Safety Letters |url=https://pubsapp.acs.org/cen/safety/19980302.html#:~:text=Filter%20paper%20strips,%20wetted%20with,alkenes,%20reacts%20quickly%20with%20phosgene. |access-date=2024-03-18 |website=pubsapp.acs.org}}</ref> There are several ] and ] reagents for phosgene, and it can also be quantified using ].<ref>{{Cite journal |last1=Cheng |first1=Xueheng |last2=Gao |first2=Quanyin |last3=Smith |first3=Richard D. |last4=Simanek |first4=Eric E. |last5=Mammen |first5=Mathai |last6=Whitesides |first6=George M. |date=1996 |title=Characterization of Hydrogen-Bonded Aggregates in Chloroform by Electrospray Ionization Mass Spectrometry |url=https://www.academia.edu/33298377 |archive-url=https://archive.today/20220731041555/https://www.academia.edu/33298377/Characterization_of_Hydrogen_Bonded_Aggregates_in_Chloroform_by_Electrospray_Ionization_Mass_Spectrometry |archive-date=2022-07-31 |url-status=live |journal=The Journal of Organic Chemistry |volume=61 |issue=6 |pages=2204–2206 |doi=10.1021/jo951345g |issn=0022-3263}}</ref>
			===Regulation===
			Chloroform is suspected of causing ] (i.e. it is possibly ]ic, ]) as per the ] (IARC) Monographs.<ref>{{Cite web |title=Chloroform |url=https://monographs.iarc.who.int/wp-content/uploads/2018/06/mono73-10.pdf |access-date=December 5, 2023}}</ref>
			It is classified as an ] in the United States, as defined in Section 302 of the US ] (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities that produce, store, or use it in significant quantities.<ref name="gov-right-know">{{Cite journal |journal = ]| publisher = ] | title = 40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities | url = http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf | edition = 1 July 2008 | access-date = 29 October 2011 | archive-url = https://web.archive.org/web/20120225051612/http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf | archive-date = 25 February 2012}}</ref>
			==Bioremediation of chloroform==
			Some ] use chloroform for respiration, termed ], converting it to ].<ref>{{cite journal|journal=Philos Trans R Soc Lond B Biol Sci|year=2013|volume=368|issue=1616|page=20120318|
			doi=10.1098/rstb.2012.0318|pmid=23479748|pmc=3638459|title=Identification of Dehalobacter reductive dehalogenases that catalyse dechlorination of chloroform, 1,1,1-trichloroethane and 1,1-dichloroethane |author=Shuiquan Tang |author2=Elizabeth A. Edwards}}</ref><ref>{{Cite journal|last1=Jugder|first1=Bat-Erdene|last2=Ertan|first2=Haluk|last3=Wong|first3=Yie Kuan|last4=Braidy|first4=Nady|last5=Manefield|first5=Michael|last6=Marquis|first6=Christopher P.|last7=Lee|first7=Matthew|date=2016-08-10|title=Genomic, transcriptomic and proteomic analyses of Dehalobacter UNSWDHB in response to chloroform|journal=Environmental Microbiology Reports|language=en|volume=8|issue=5|pages=814–824|doi=10.1111/1758-2229.12444|pmid=27452500|bibcode=2016EnvMR...8..814J |issn=1758-2229}}</ref>
			==Gallery==
			<gallery>
			File:CHCl3 mm.png|{{chem2|CHCl3}} measured by the Advanced Global Atmospheric Gases Experiment () in the lower atmosphere (]) at stations around the world. Abundances are given as pollution free monthly mean mole fractions in ] (ppt).
			</gallery>
			== See also ==
			* ]
			== References ==
			{{Reflist}}
	==External links==		==External links==
			{{Commons category|Chloroform}}
	* An article at Oxford University providing facts about chloroform.
			* – An article at Oxford University providing facts about chloroform.
			* – a short film of anaesthetic chloroform application, filmed in the 1930s
	*		*
	*
	*IARC Summaries & Evaluations: , , ,		*IARC Summaries & Evaluations: , , ,
	*{{ICSC|0027|00}}		*{{ICSC|0027|00}}
	*{{PGCH|0127}}		*{{PGCH|0127}}
	*
	*		*
	* from BBC's The Material World (28 July 2005)
	* article at Carolina Poison Center
	*Calculation of , , , of chloroform
	*
	<!--spacing-->
	{{General anesthetics}}
	{{Halomethanes}}		{{Halomethanes}}
			{{General anesthetics}}
	{{Use dmy dates|date=September 2010}}
			{{Hallucinogens}}
			{{Navboxes
			| title = ]
			| titlestyle = background:#ccccff
			| list1 =
			{{GABAA receptor positive modulators}}
			{{Ionotropic glutamate receptor modulators}}
			{{Glycine receptor modulators}}
			}}
			{{Chloroform committees and commissions}}
			{{Authority control}}
	]		]
	]		]
	]		]
	]		]
	]		]
	]
	]		]
			]
			]
	]
			]
	]
			]
	]
			]
	]
			]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]
	]