| Revision as of 17:16, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 444028803 of page 2-Chloroethanol for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 14:40, 25 January 2023 edit Zakblade2000 (talk | contribs)Extended confirmed users4,108 editsNo edit summary |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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|Verifiedfields = changed |
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| verifiedrevid = 443345388 |
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|Watchedfields = changed |
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| Name = 2-Chloroethanol |
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|verifiedrevid = 477213021 |
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| ImageFile = 2-chloroethanol-skeletal-nu.png |
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|ImageFile = 2-Chloroethanol-2D-by-AHRLS-2012.png |
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|ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile1 = 2-chloroethanol-3D-balls.png |
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|ImageSize = 100 |
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<!-- | ImageSize1 = 150px --> |
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|ImageName = Skeletal formula of 2-chloroethanol |
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| IUPACName = 2-Chloroethanol |
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|ImageFileL1 = 2-chloroethanol-3D-balls.png |
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| OtherNames = 2-chloroethyl alcohol, ethylene chlorohydrin, glycol chlorohydrin, 2-chloro-1-ethanol, 2-monochloroethanol, 2-hydroxyethyl chloride, β-chloroethanol, β-hydroxyethyl chloride, chloroethanol, δ-chloroethanol, ethylchlorhydrin, ethylene chlorohydrin, glycol monochlorohydrin |
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|ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| Section1 = {{Chembox Identifiers |
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|ImageNameL1 = Ball and stick model of 2-chloroethanol |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ImageFileR1 = 2-chloroethanol-3D-vdW.png |
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| ChemSpiderID = 21106015 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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|ImageFileR1_Ref = {{chemboximage|correct|??}} |
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|ImageNameR1 = Spacefill model of 2-chloroethanol |
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| KEGG = C06753 |
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|PIN = 2-Chloroethan-1-ol<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 29 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4 | quote = For example, the omission of the locant ‘1’ in 2-chloroethanol, while permissible in general usage, is not allowed in preferred IUPAC names, thus the name 2-chloroethan-1-ol is the PIN.}}</ref> |
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| InChI = 1/C2H5ClO/c3-1-2-4/h4H,1-2H2 |
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|OtherNames = {{unbulleted list |
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| InChIKey = SZIFAVKTNFCBPC-UHFFFAOYAF |
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| 2-Chloroethanol<ref name=iupac2013/> |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ''beta''-Chloroethanol<ref name="pubchem" >.</ref> |
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| ChEMBL = 191244 |
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| 2-Chloro-1-ethanol<ref name="pubchem" /> |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| β-Chloroethanol<ref name="pubchem" /> |
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| StdInChI = 1S/C2H5ClO/c3-1-2-4/h4H,1-2H2 |
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| δ-Chloroethanol<ref name="pubchem" /> |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| 2-Chloroethyl alcohol<ref name="pubchem" /> |
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| StdInChIKey = SZIFAVKTNFCBPC-UHFFFAOYSA-N |
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| Ethyl chlorhydrin<ref name="pubchem" /> |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| Ethylene chlorohydrin<ref name="pubchem" /> |
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| CASNo = 107-07-3 |
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| Glycol chlorohydrin<ref name="pubchem" /> |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| Glycol monochlorohydrin<ref name="pubchem" /> |
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| ChEBI = 28200 |
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| 2-Hydroxyethyl chloride<ref name="pubchem" /> |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| β-Hydroxyethyl chloride<ref name="pubchem" /> |
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| UNII = 753N66IHAN |
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| 2-Monochloroethanol<ref name="pubchem" /> |
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| SMILES = ClCCO |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section1={{Chembox Identifiers |
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|CASNo = 107-07-3 |
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| Formula = C<sub>2</sub>H<sub>5</sub>ClO |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| MolarMass = 80.52 g/mol |
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|PubChem = 34 |
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| Density = 1.197 g/cm³ |
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|ChemSpiderID = 21106015 |
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| MeltingPt = -67 °C |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| BoilingPt = 128-130 °C |
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|UNII = 753N66IHAN |
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}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| Section8 = {{Chembox Related |
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|EINECS = 203-459-7 |
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| OtherCpds = ] |
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|UNNumber = 1135 |
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}} |
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|KEGG = C06753 |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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|MeSHName = Ethylene+Chlorohydrin |
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|ChEBI = 28200 |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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|ChEMBL = 191244 |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|RTECS = KK0875000 |
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|Beilstein = 878139 |
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|Gmelin = 25389 |
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|3DMet = B01042 |
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|SMILES = OCCCl |
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|StdInChI = 1S/C2H5ClO/c3-1-2-4/h4H,1-2H2 |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = SZIFAVKTNFCBPC-UHFFFAOYSA-N |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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}} |
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|Section2={{Chembox Properties |
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|C=2 | H=5 | Cl=1 | O=1 |
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|Appearance = Colourless liquid |
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|Odor = ]-like |
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|Density = 1.201 g/mL |
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|MeltingPtK = 210.55 |
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|BoilingPtK = 400–404 |
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|LogP = −0.107 |
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|VaporPressure = 700 Pa (at 20 °C) |
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|RefractIndex = 1.441 |
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|Solubility = Miscible<ref name=PGCH/> |
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}} |
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|Section3={{Chembox Thermochemistry |
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|DeltaHc = −1.1914 MJ/mol |
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}} |
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|Section4={{Chembox Hazards |
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|MainHazards = Highly toxic and flammable |
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|GHSPictograms = {{gHS flame}} {{gHS skull and crossbones}} |
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|GHSSignalWord = '''DANGER''' |
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|HPhrases = {{h-phrases|226|300+310+330}} |
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|PPhrases = {{p-phrases|260|280|284|301+310|302+350}} |
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|NFPA-H = 4 |
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|NFPA-F = 2 |
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|NFPA-R = 0 |
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|FlashPtC = 55 |
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|AutoignitionPtC = 425 |
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|ExploLimits = 5–16% |
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|LD50 = {{ubl |
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| 67{{nbsp}}mg/kg <small>(dermal, rabbit)</small>{{citation needed|date=June 2015}} |
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| 72{{nbsp}}mg/kg (rat, oral) |
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| 81{{nbsp}}mg/kg (mouse, oral) |
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| 71{{nbsp}}mg/kg (rat, oral) |
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| 110{{nbsp}}mg/kg (guinea pig, oral)<ref name=IDLH>{{IDLH|107073|Ethylene chlorohydrin}}</ref> |
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}} |
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|LC50 = {{ubl |
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| 7.5{{nbsp}}ppm (rat, 1{{nbsp}}]) |
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| 32{{nbsp}}ppm (rat, 4{{nbsp}}h) |
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| 260{{nbsp}}ppm (guinea pig) |
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| 33{{nbsp}}ppm (rat, 4{{nbsp}}h) |
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| 87{{nbsp}}ppm (rat) |
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| 115{{nbsp}}ppm (mouse)<ref name=IDLH/> |
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|PEL = TWA 5{{nbsp}}ppm (16{{nbsp}}mg/m<sup>3</sup>) <ref name=PGCH>{{PGCH|0268}}</ref> |
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|REL = C 1{{nbsp}}ppm (3{{nbsp}}mg/m<sup>3</sup>) <ref name=PGCH/> |
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|IDLH = 7{{nbsp}}ppm<ref name=PGCH/> |
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}}<ref>{{Cite web |url=http://www.newenv.com/resources/nfpa_chemicals |website=New Environment Inc. |title=NFPA Chemicals}}</ref> |
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|Section5={{Chembox Related |
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| OtherCompounds = {{unbulleted list |
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'''2-Chloroethanol''' (also called '''ethylene chlorohydrin''' or '''glycol chlorohydrin''') is an organic ] with the ] HOCH<sub>2</sub>CH<sub>2</sub>Cl and the ''simplest'' ] (chlorohydrin).<ref>Ethylene chlorohydrin: properties</ref> This colorless liquid has a pleasant ether-like odor. It is miscible with water. The molecule is bifunctional, consisting of both an ] and an ] ].<ref name=Ullmann/> |
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==Synthesis and applications== |
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2-Chloroethanol is produced by treating ] with ]:<ref name=Ullmann/> |
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:] |
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2-Chloroethanol was once produced on a large scale as a precursor to ]: |
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:] |
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:HOCH<sub>2</sub>CH<sub>2</sub>Cl + NaOH → C<sub>2</sub>H<sub>4</sub>O + NaCl + H<sub>2</sub>O |
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This application has been supplanted by the more economic direct ] of ]. Otherwise chloroethanol is still used in the production of ]s, ]s, and ]s.<ref name=Ullmann>{{Ullmann|first1=Gordon Y. T.|last1=Liu|first2=W. Frank|last2=Richey|first3=Joanne E.|last3=Betso|first4=Brian |last4=Hughes|first5=Joanna|last5=Klapacz|first6=Joerg |last6=Lindner|display-authors=3|title=Chlorohydrins|year=2014|doi= 10.1002/14356007.a06_565.pub2}}</ref> Many of these applications entail its use in installing 2-hydroxyethyl groups.<ref>{{cite journal|journal=Organic Syntheses|author1=Butler J|author2 = Kellogg R|title=Synthesis of Macrocyclic Sulfides Using Cesium Thiolates: 1,4,8,11-Tetrathiacyclotetradecane|year=1987|volume=65|issue=150|page=150|doi=10.15227/orgsyn.065.0150}}</ref> Several ]s are prepared by the ] of ] derivatives with chloroethanol.<ref>{{Ullmann|first1=Roderich|last1=Raue|first2=John F.|last2=Corbett|title=Nitro and Nitroso Dyes|year=2002|doi=10.1002/14356007.a17_383}}</ref> It is also used for manufacture of ]. |
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It is a ] for ] and ], textile printing dyes, in dewaxing, refining of ], extraction of ] ], and the cleaning of machines. |
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==Environmental aspects== |
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Chloroethanol is a ] in the degradation of ]. The alcohol is then further oxidized via ] to chloroacetate. This metabolic pathway is topical since billions of kilograms of 1,2-dichloroethane are processed annually as a precursor to ].<ref>{{cite journal | last1 = Janssen | first1 = D. B. | last2 = van der Ploeg | first2 = J. R. | last3 = Pries | first3 = F. | year = 1994 | title = Genetics and Biochemistry of 1,2-Dichloroethane Degradation | url = https://pure.rug.nl/ws/files/14528144/1994BiodegradJanssen.pdf| journal = Biodegradation | volume = 5 | issue = 3–4| pages = 249–57 | doi = 10.1007/BF00696463 | pmid = 7765836 | s2cid = 475768}}</ref> |
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==Safety== |
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2-Chloroethanol is toxic with an {{LD50}} of 89 mg/kg in rats. Like most organochlorine compounds, chloroethanol releases ] and ] when burned. |
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In regards to dermal exposure to 2-chloroethanol, the ] has set a ] of 5{{nbsp}}ppm (16{{nbsp}}mg/m<sup>3</sup>) over an eight-hour time-weighted average, while the ] has a more protective ] of a 1{{nbsp}}ppm (3{{nbsp}}mg/m<sup>3</sup>) exposure ceiling.<ref></ref> |
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It is classified as an ] in the United States as defined in Section 302 of the U.S. ] (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.<ref>{{Cite book |publisher=] |title=Code of Federal Regulations |section=40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities |section-url=http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf |edition=July 1, 2008 |access-date=October 29, 2011 |archive-url=https://web.archive.org/web/20120225051612/http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf |archive-date=February 25, 2012}}</ref>{{failed verification|date=February 2020}} |
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==References== |
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{{reflist}} |
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{{Authority control}} |
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{{DEFAULTSORT:Chloroethanol, 2-}} |
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] |
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