View source for Chemistry:1,2-Dibromoethane

{{Chembox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 477203333
|ImageFile2 = 1,2-dibromoethane-3D-vdW.png
|ImageFile2_Ref = {{chemboximage|correct|??}}
|ImageSize2 = 100
|ImageName2 = Spacefill model of 1,2-dibromoethane
|ImageFileL1 = 1,2-Dibromoethane v2.svg
|ImageSizeL1 = 150
|ImageFileL1_Ref = {{chemboximage|correct|??}}
|ImageNameL1 = Skeletal formula of 1,2-dibromoethane
|ImageFileR1 = Valence structural formula of 1,2-dibromoethane.svg
|ImageSizeR1 = 150
|ImageFileR1_Ref = {{chemboximage|correct|??}}
|ImageNameR1 = Skeletal formula of 1,2-dibromoethane with all explicit hydrogens added
|PIN = 1,2-Dibromoethane<ref name=iupac2013>{{cite book | title =  Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Organization:Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 657 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref>
|OtherNames = {{Unbulleted list|Ethylene dibromide<ref name=iupac2013 />|Ethylene bromide<ref name=PGCH />|Glycol bromide<ref name=PGCH />|Di(bromomethyl)
}}
|Section1 = {{Chembox Identifiers
|Abbreviations = EDB{{Citation needed|date=June 2012}}
|CASNo = 106-93-4
|CASNo_Ref = {{cascite|correct|CAS}}
|UNII_Ref = {{fdacite|changed|FDA}}
|UNII = 1N41638RNO
|PubChem = 7839
|ChemSpiderID = 7551
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|EINECS = 203-444-5
|UNNumber = 1605
|KEGG = C11088
|KEGG_Ref = {{keggcite|correct|kegg}}
|MeSHName = Ethylene+Dibromide
|ChEBI = 28534
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEMBL = 452370
|ChEMBL_Ref = {{ebicite|correct|EBI}}
|RTECS = KH9275000
|Beilstein = 605266
|SMILES = BrCCBr
|StdInChI = 1S/C2H4Br2/c3-1-2-4/h1-2H2
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = PAAZPARNPHGIKF-UHFFFAOYSA-N
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2 = {{Chembox Properties
|C=2 | H=4 | Br=2
|Appearance = Colorless liquid
|Odor = faintly sweet<ref name=PGCH/>
|Density = 2.18 g mL{{sup|−1}}
|MeltingPtK = 282.5 to 283.3
|BoilingPtK = 402 to 406
|LogP = 2.024
|VaporPressure = 1.56 kPa
|HenryConstant = 14 μmol Pa kg{{sup|−1}}
|RefractIndex = 1.539
|Solubility = 0.4% (20&nbsp;°C)<ref name=PGCH/>
}}
|Section3 = {{Chembox Thermochemistry
|DeltaHc = −1.2419–−1.2387 MJ mol{{sup|−1}}
|Entropy = 223.30 J K{{sup|−1}} mol{{sup|−1}}
|HeatCapacity = 134.7 J K{{sup|−1}} mol{{sup|−1}}
}}
|Section4 = {{Chembox Hazards
|GHSPictograms = {{GHS skull and crossbones}} {{GHS health hazard}} {{GHS environment}}
|GHSSignalWord = '''DANGER'''
|HPhrases = {{H-phrases|301|311|315|319|331|335|350|411}}
|PPhrases = {{P-phrases|261|273|280|301+310|305+351+338}}
|NFPA-H = 3  
|NFPA-F = 0
|NFPA-R = 0
|FlashPtC = 104
|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>}}
|PEL = TWA 20 ppm C 30 ppm 50 ppm [5-minute maximum peak]<ref name=PGCH>{{PGCH|0270}}</ref>
|IDLH = Ca [100 ppm]<ref name=PGCH/>
|MainHazards = carcinogen<ref name=PGCH/>
|REL = Ca TWA 0.045 ppm C 0.13 ppm [15-minute]<ref name=PGCH/>
|LC50 = 1831 ppm (rat, 30 min)<br/>691 ppm (rat, 1 hr)<ref name=IDLH>{{IDLH|106934|Ethylene dibromide}}</ref>
|LCLo = 200 ppm (rat, 8 hr)<br/>400 ppm (guinea pig, 3 hr)<ref name=IDLH/>
}}
|Section5 = {{Chembox Related
|OtherFunction_label = alkanes
|OtherFunction = {{Unbulleted list|[[Chemistry:Dibromomethane|Dibromomethane]]|[[Chemistry:Bromoform|Bromoform]]|[[Chemistry:Tetrabromomethane|Tetrabromomethane]]|[[Chemistry:1,1-Dibromoethane|1,1-Dibromoethane]]|[[Chemistry:Tetrabromoethane|Tetrabromoethane]]|[[Chemistry:1,2-Dibromopropane|1,2-Dibromopropane]]|[[Chemistry:1,3-Dibromopropane|1,3-Dibromopropane]]|[[Chemistry:1,2,3-Tribromopropane|1,2,3-Tribromopropane]]}}
}}
}}
'''1,2-Dibromoethane''', also known as '''ethylene dibromide''' ('''EDB'''), is an [[Chemistry:Organobromine compound|organobromine compound]] with the [[Chemistry:Chemical formula|chemical formula]] {{chem|C|2|H|4|Br|2}}. Although trace amounts occur naturally in the [[Earth:Ocean|ocean]], where it is probably formed by [[Biology:Algae|algae]] and [[Biology:Kelp|kelp]], it is mainly synthetic. It is a dense colorless liquid with a faint, sweet odor, detectable at 10 ppm, and is a widely used and sometimes-controversial fumigant.<ref name=Ullmann/> The combustion of 1,2-dibromoethane produces [[Chemistry:Hydrogen bromide|hydrogen bromide]] 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>

==Preparation and use==
It is produced by the reaction of [[Chemistry:Ethylene|ethylene]] gas with [[Chemistry:Bromine|bromine]],<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 [[Chemistry:Halogen addition reaction|halogen addition reaction]]:
:CH{{sub|2}}=CH{{sub|2}} + Br{{sub|2}} → BrCH{{sub|2}}–CH{{sub|2}}Br

Historically, 1,2-dibromoethane was used as a component in anti-knock [[Chemistry:List of gasoline additives|additives]] 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 = [[Chemistry:Organometallics|Organometallics]] | year = 2003 | volume = 22 | issue = 25 | pages = 5154–5178 | doi = 10.1021/om030621b | doi-access =  }}</ref>

===Pesticide===
It has been used as a [[Biology:Pesticide|pesticide]] in [[Chemistry:Soil|soil]] and on various crops.  The applications were initiated after the forced retirement of 1,2-dibromo-3-chloropropane (DBCP).<ref name=Ullmann>{{Ullmann | author = Dagani, M. J. | author2 = Barda, H. J. | author3 = Benya, T. J. | author4 = Sanders, D. C. | title = Bromine Compounds | doi = 10.1002/14356007.a04_405}}</ref> Most of these uses have been stopped in the U.S. It continues to be used as a fumigant for treatment of logs for [[Biology:Termite|termite]]s and [[Biology:Beetle|beetle]]s, and for control of [[Biology:Moth|moth]]s in beehives.<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>

===Reagent===
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 [[Chemistry:Fire retardant|fire retardant]]s.<ref name=Ullmann/>

In [[Chemistry:Organic synthesis|organic synthesis]], 1,2-dibromoethane is used as a source of bromine to brominate [[Chemistry:Carbanion|carbanion]]s and to activate [[Chemistry:Magnesium|magnesium]] for certain [[Chemistry:Grignard reagent|Grignard reagent]]s. In the latter process, 1,2-dibromoethane reacts with magnesium, producing ethene and [[Chemistry:Magnesium bromide|magnesium bromide]], and exposes a freshly etched portion of magnesium 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>

==Health effects==
1,2-Dibromoethane causes changes in the [[Biology:Metabolism|metabolism]] and severe destruction of living tissues.<ref name=":0" /> The known empirical LD50 values for 1,2-dibromoethane are 140&nbsp;mg kg<sup>−1</sup> (oral, rat), and 300.0&nbsp;mg kg<sup>−1</sup> (dermal, rabbit).<ref name=":0" /> 1,2-Dibromoethane is a known [[Biology:Carcinogen|carcinogen]], 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>

The effects 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 [[Medicine:Birth defect|birth defect]]s in humans. Swallowing has caused death at 40ml doses.<ref name="www.atsdr.cdc.gov" />

==References==
{{Reflist}}

==External links==
* [https://web.archive.org/web/20060125030149/http://www.npi.gov.au/database/substance-info/profiles/31.html National Pollutant Inventory 1,2-Dibromoethane Fact Sheet]
* [https://web.archive.org/web/20080315175144/http://digital.library.unt.edu/govdocs/crs/search.tkl?q=ethylene+dibromide&search_crit=title&search=Search&date1=Anytime&date2=Anytime&type=form Congressional Research Service (CRS) Reports regarding Ethylene Dibromide]
* [https://wwwn.cdc.gov/TSP/ToxFAQs/ToxFAQsLanding.aspx?id=725&tid=131 ATSDR ToxFAQs]
* [https://www.cdc.gov/niosh/npg/npgd0270.html CDC – NIOSH Pocket Guide to Chemical Hazards]

{{Motor fuel}}

{{DEFAULTSORT:Dibromoethane, 1, 2-}}
[[Category:Endocrine disruptors]]
[[Category:Insecticides]]
[[Category:Bromoalkanes]]
[[Category:Fumigants]]
[[Category:Hazardous air pollutants]]
[[Category:IARC Group 2A carcinogens]]

{{Sourceattribution|1,2-Dibromoethane}}