| Revision as of 16:09, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 473409819 of page 1,2-Dibromoethane for the Chem/Drugbox validation project (updated: ''). |
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{{Chembox |
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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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| Verifiedfields = changed |
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|Watchedfields = changed |
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| verifiedrevid = 456360796 |
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|verifiedrevid = 477203333 |
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|ImageFile2 = 1,2-dibromoethane-3D-vdW.png |
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| Name = 1,2-Dibromoethane |
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|ImageFile2_Ref = {{chemboximage|correct|??}} |
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| ImageFileL1 = 1,2-dibromoethane.svg |
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|ImageSize2 = 100 |
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| ImageSizeL1 = 120px |
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|ImageName2 = Spacefill model of 1,2-dibromoethane |
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| ImageNameL1 = 1,2-Dibromoethane |
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|ImageFileL1 = 1,2-Dibromoethane v2.svg |
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| ImageFileR1 = 1,2-dibromoethane-3D-vdW.png |
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|ImageSizeL1 = 150 |
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| ImageSizeR1 = 120px |
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|ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageNameR1 = 1,2-Dibromoethane |
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| IUPACName = 1,2-dibromoethane |
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|ImageNameL1 = Skeletal formula of 1,2-dibromoethane |
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|ImageFileR1 = Valence structural formula of 1,2-dibromoethane.svg |
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| OtherNames = ethylene dibromide<br />ethylene bromide<br />EDB<br />glycol bromide<br />ethylene bromide,<br/> Bromofume (trade name),<br/>Dowfume (trade name) |
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|ImageSizeR1 = 150 |
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| Section1 = {{Chembox Identifiers |
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|ImageFileR1_Ref = {{chemboximage|correct|??}} |
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| SMILES = BrCCBr |
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|ImageNameR1 = Skeletal formula of 1,2-dibromoethane with all explicit hydrogens added |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|PIN = 1,2-Dibromoethane<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 657 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref> |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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|OtherNames = {{Unbulleted list|Ethylene dibromide<ref name=iupac2013 />|Ethylene bromide<ref name=PGCH />|Glycol bromide<ref name=PGCH />|Di(bromomethyl) |
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| ChEBI = 28534 |
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| ChemSpiderID = 7551 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C11088 |
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| InChI = 1/C2H4Br2/c3-1-2-4/h1-2H2 |
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| InChIKey = PAAZPARNPHGIKF-UHFFFAOYAZ |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 452370 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C2H4Br2/c3-1-2-4/h1-2H2 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = PAAZPARNPHGIKF-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 106-93-4 |
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| RTECS = KH9275000 |
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}} |
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| Section2 = {{Chembox Properties |
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| Formula = ''']'''<sub>2</sub>''']'''<sub>4</sub>''']'''<sub>2</sub> |
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| MolarMass = 187.86 g/mol |
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| Appearance = colorless liquid |
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| Density = 2.17 g/cm³, liquid |
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| Solubility = 1 part in 250 |
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| MeltingPt = 9-10 °C |
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| BoilingPt = 131-132 °C |
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}} |
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| Section7 = {{Chembox Hazards |
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| MainHazards = |
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| NFPA-H = 3 |
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| NFPA-F = |
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| NFPA-R = |
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| FlashPt = >104 °C |
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| RPhrases = {{R45}}, {{R23/24/25}},<br /> {{R36/37/38}}, {{R51/53}} |
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| SPhrases = {{S53}}, {{S45}}, {{S61}} |
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}} |
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| Section8 = {{Chembox Related |
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| Function = ]s |
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| OtherFunctn = ]<br />] |
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| OtherCpds = ] |
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}} |
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}} |
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}} |
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|Section1 = {{Chembox Identifiers |
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|Abbreviations = EDB{{Citation needed|date=June 2012}} |
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|CASNo = 106-93-4 |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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|UNII_Ref = {{fdacite|changed|FDA}} |
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|UNII = 1N41638RNO |
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|PubChem = 7839 |
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|ChemSpiderID = 7551 |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|EINECS = 203-444-5 |
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|UNNumber = 1605 |
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|KEGG = C11088 |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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|MeSHName = Ethylene+Dibromide |
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|ChEBI = 28534 |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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|ChEMBL = 452370 |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|RTECS = KH9275000 |
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|Beilstein = 605266 |
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|SMILES = BrCCBr |
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|StdInChI = 1S/C2H4Br2/c3-1-2-4/h1-2H2 |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = PAAZPARNPHGIKF-UHFFFAOYSA-N |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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}} |
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|Section2 = {{Chembox Properties |
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|C=2 | H=4 | Br=2 |
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|Appearance = Colorless liquid |
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|Odor = faintly sweet<ref name=PGCH/> |
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|Density = 2.18 g mL{{sup|−1}} |
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|MeltingPtK = 282.5 to 283.3 |
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|BoilingPtK = 402 to 406 |
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|LogP = 2.024 |
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|VaporPressure = 1.56 kPa |
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|HenryConstant = 14 μmol Pa kg{{sup|−1}} |
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|RefractIndex = 1.539 |
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|Solubility = 0.4% (20 °C)<ref name=PGCH/> |
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}} |
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|Section3 = {{Chembox Thermochemistry |
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|DeltaHc = −1.2419–−1.2387 MJ mol{{sup|−1}} |
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|Entropy = 223.30 J K{{sup|−1}} mol{{sup|−1}} |
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|HeatCapacity = 134.7 J K{{sup|−1}} mol{{sup|−1}} |
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}} |
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|Section4 = {{Chembox Hazards |
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|GHSPictograms = {{GHS skull and crossbones}} {{GHS health hazard}} {{GHS environment}} |
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|GHSSignalWord = '''DANGER''' |
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|HPhrases = {{H-phrases|301|311|315|319|331|335|350|411}} |
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|PPhrases = {{P-phrases|261|273|280|301+310|305+351+338}} |
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|NFPA-H = 3 |
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|NFPA-F = 0 |
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|NFPA-R = 0 |
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|FlashPtC = 104 |
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|LD50 = {{Unbulleted list|55.0 mg kg{{sup|−1}} <small>(oral, rabbit)</small>|79.0 mg kg{{sup|−1}} <small>(oral, chicken)</small>|110.0 mg kg{{sup|−1}} <small>(oral, guinea pig)</small>|130.0 mg kg{{sup|−1}} <small>(oral, quail)</small>|300.0 mg kg{{sup|−1}} <small>(dermal, rabbit)</small>}} |
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|PEL = TWA 20 ppm C 30 ppm 50 ppm <ref name=PGCH>{{PGCH|0270}}</ref> |
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|IDLH = Ca <ref name=PGCH/> |
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|MainHazards = carcinogen<ref name=PGCH/> |
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|REL = Ca TWA 0.045 ppm C 0.13 ppm <ref name=PGCH/> |
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|LC50 = 1831 ppm (rat, 30 min)<br/>691 ppm (rat, 1 hr)<ref name=IDLH>{{IDLH|106934|Ethylene dibromide}}</ref> |
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|LCLo = 200 ppm (rat, 8 hr)<br/>400 ppm (guinea pig, 3 hr)<ref name=IDLH/> |
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}} |
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|Section5 = {{Chembox Related |
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|OtherFunction_label = alkanes |
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|OtherFunction = {{Unbulleted list|]|]|]|]|]|]|]|]}} |
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}} |
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}} |
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'''1,2-Dibromoethane''', also known as '''ethylene dibromide''' ('''EDB'''), is an ] with the ] {{chem|C|2|H|4|Br|2}}. Although trace amounts occur naturally in the ], where it is probably formed by ] and ], substantial amounts are produced industrially. It is a dense colorless liquid with a faint, sweet odor, detectable at 10 ppm. It is a widely used and sometimes-controversial ].<ref name=Ullmann/> The combustion of 1,2-dibromoethane produces ] gas that is significantly corrosive.<ref name=":0">{{Cite web|url=https://www.sigmaaldrich.com|title=Safety Data Sheet for CAS-No.:106-93-4 Ethylene dibromide}}</ref> |
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==Preparation and use== |
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It is produced by the reaction of ] gas with ],<ref>{{Cite journal|date=2017|title=Preparation and purification of 1,2-dibromoethane|url=https://www.thieme-connect.de/media/synlett/201713/supmat/sup_st-2017-b0194-l_10-1055_s-0036-1588180.pdf|journal=Synlett|volume=28|pages=49–51}}</ref> in a classic ]: |
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:CH{{sub|2}}=CH{{sub|2}} + Br{{sub|2}} → BrCH{{sub|2}}–CH{{sub|2}}Br |
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Historically, 1,2-dibromoethane was used as a component in anti-knock ] in leaded fuels. It reacts with lead residues to generate volatile lead bromides, thereby preventing fouling of the engine with lead deposits.<ref>{{cite journal | author = Seyferth, D. | title = The Rise and Fall of Tetraethyllead. 2 | journal = ] | year = 2003 | volume = 22 | issue = 25 | pages = 5154–5178 | doi = 10.1021/om030621b | doi-access = }}</ref> |
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===Pesticide=== |
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It has been used as a ] in ] and on various crops. The applications were initiated after the forced retirement of ] (DBCP).<ref name=Ullmann>{{cite book| doi = 10.1002/14356007.a04_405.pub2| chapter = Bromine Compounds| title = Ullmann's Encyclopedia of Industrial Chemistry| date = 2013| last1 = Yoffe| first1 = David| last2 = Frim| first2 = Ron| last3 = Ukeles| first3 = Shmuel D.| last4 = Dagani| first4 = Michael J.| last5 = Barda| first5 = Henry J.| last6 = Benya| first6 = Theodore J.| last7 = Sanders| first7 = David C.| pages = 1–31| isbn = 978-3-527-30385-4}}</ref> Most of these uses have been stopped in the U.S. It continues to be used as a ] for treatment of logs for ]s and ]s, and for control of ]s in ].<ref name="www.atsdr.cdc.gov">{{cite web | url = http://www.atsdr.cdc.gov/toxprofiles/tp37.pdf | title = Toxicological Profile for 1,2-Dibromoethane | access-date = 2009-11-22 | archive-url = https://web.archive.org/web/20091122182238/http://www.atsdr.cdc.gov/toxprofiles/tp37.pdf | archive-date = 2009-11-22}}</ref> |
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===Reagent=== |
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1,2-Dibromoethane has wider applications in the preparation of other organic compounds including those carrying modified diazocine rings<ref>{{Cite journal|author1=Hamada, Y.|author2= Mukai. S.|date=1996|title=Synthesis of ethano-Tröger's base, configurationally stable substitute of Tröger's base |journal=Tetrahedron Asymmetry|volume=7|issue=9|pages=2671–2674|doi=10.1016/0957-4166(96)00343-6}}</ref> and vinyl bromide that is a precursor to some ]s.<ref name=Ullmann/> |
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In ], 1,2-dibromoethane is used to brominate ]s and to activate ] for certain ]s. In the latter process, 1,2-dibromoethane reacts with magnesium, producing ] and ], which are innocuous, exposing a more active portion of the magnesium particle to the substrate.<ref>{{ cite encyclopedia | author = Maynard, G. D. | chapter = 1,2-Dibromoethane | encyclopedia = Encyclopedia of Reagents for Organic Synthesis | editor = Paquette, L. | year = 2004 | publisher = J. Wiley & Sons | location = New York | doi = 10.1002/047084289X.rd039 | isbn = 0471936235}}</ref> |
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==Health effects== |
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1,2-Dibromoethane causes changes in the ] and severe destruction of living tissues.<ref name=":0" /> The known empirical LD50 values for 1,2-dibromoethane are 140 mg kg<sup>−1</sup> (oral, rat), and 300.0 mg kg<sup>−1</sup> (dermal, rabbit).<ref name=":0" /> 1,2-Dibromoethane is a known ], with pre-1977 exposure levels ranking it as the most carcinogenic substance on the HERP Index.<ref>{{Cite web|url=https://toxnet.nlm.nih.gov/cpdb/pdfs/herp.pdf |archive-url=https://web.archive.org/web/20190629174358/https://toxnet.nlm.nih.gov/cpdb/pdfs/herp.pdf |archive-date=2019-06-29 |title=Ranking Possible Cancer Hazards from Rodent Carcinogens}}</ref> |
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The ] on people of breathing high levels are not known, but animal studies with short-term exposures to high levels caused depression and collapse, indicating effects on the brain. Changes in the brain and behavior were also seen in young rats whose male parents had breathed 1,2-dibromoethane, and birth defects were observed in the young of animals that were exposed while pregnant.<ref>{{Cite web|url=https://www.atsdr.cdc.gov/mmg/mmg.asp?id=1062&tid=131|title=Toxic Substances Portal – 1,2-Dibromoethane}}</ref> 1,2-Dibromoethane is not known to cause ]s in humans. Swallowing has caused death at 40ml doses.<ref name="www.atsdr.cdc.gov" /> |
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==References== |
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{{Reflist}} |
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==External links== |
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{{Motor fuel}} |
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{{Authority control}} |
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{{DEFAULTSORT:Dibromoethane, 1, 2-}} |
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