1,2-Dibromoethane 241806 224187367 2008-07-07T18:46:08Z 90.192.52.155 /* Uses */ {{Chembox new | Name = 1,2-Dibromoethane | ImageFileL1 = 1,2-dibromoethane.svg | ImageSizeL1 = 120px | ImageNameL1 = 1,2-Dibromoethane | ImageFileR1 = 1,2-dibromoethane-3D-vdW.png | ImageSizeR1 = 120px | ImageNameR1 = 1,2-Dibromoethane | IUPACName = 1,2-dibromoethane | OtherNames = ethylene dibromide<br />ethylene bromide<br />EDB<br />glycol bromide<br />ethylene bromide,<br/> Bromofume (trade name),<br/>Dowfume (trade name) | Section1 = {{Chembox Identifiers | SMILES = C(Br)CBr | CASNo = 106-93-4 | RTECS = KH9275000 }} | Section2 = {{Chembox Properties | Formula = '''[[Carbon|C]]'''<sub>2</sub>'''[[Hydrogen|H]]'''<sub>4</sub>'''[[Bromine|Br]]'''<sub>2</sub> | MolarMass = 187.86 g/mol | Appearance = colorless liquid | Density = 2.17 g/cm³, liquid | Solubility = 1 part in 250 | MeltingPt = 9-10 °C | BoilingPt = 131-132 °C }} | Section7 = {{Chembox Hazards | MainHazards = | NFPA-H = 3 | NFPA-F = | NFPA-R = | FlashPt = >104 °C | RPhrases = {{R45}}, {{R23/24/25}},<br /> {{R36/37/38}}, {{R51/53}} | SPhrases = {{S53}}, {{S45}}, {{S61}} }} | Section8 = {{Chembox Related | Function = [[organobromide]]s | OtherFunctn = [[bromoethane]]<br />[[1,1-dibromoethane]] | OtherCpds = [[1,2-Dichloroethane|1,2-dichloroethane]] }} }} '''1,2-Dibromoethane''' is the [[chemical compound]] with the formula [[Bromine|Br]][[Carbon|C]][[Hydrogen|H]]<sub>2</sub>[[Carbon|C]][[Hydrogen|H]]<sub>2</sub>[[Bromine|Br]]. Although trace amounts occurs naturally in the [[ocean]], where it is formed probably by [[algae]] and [[kelp]], it is mainly a synthetic. It is a colorless liquid with a mild, sweaty odor. ==Preparation and structure== It is manufactured by the reaction of [[ethylene]] with [[bromine]]: :CH<sub>2</sub>=CH<sub>2</sub> + Br<sub>2</sub> → BrCH<sub>2</sub>CH<sub>2</sub>Br ==Uses== 1,2-Dibromoethane is used in [[organic synthesis]] as an "entrainment reagent" to activate [[magnesium]] for certain [[Grignard reagent]]s. In this process, the 1,2-dibromoethane is converted to ethylene and magnesium bromide, exposing a freshly etched portion of magnesium to the substrate.<ref>Maynard, G. D. "1,2-Dibromoethane" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. DOI: 10.1002/047084289.</ref> 1,2-Dibromoethane is a precursor to many 1,2-disubstituted ethane derivatives, e.g. [[1,2-Ethanedithiol|1,2-ethanedithiol]]. In some cases, 1,2-dibromoethane is used to brominate carbanions. Another major use, although one that is fading in importance, is as an additive in leaded [[gasoline]]. ===As a pesticide and fumigant=== 1,2-Dibromoethane has been used as a [[pesticide]] in [[soil]], and on [[citrus]], [[vegetable]], and [[cereal]] crops. Most of these uses have been stopped by the [[United States Environmental Protection Agency]] (EPA) since 1984. Uses today include a [[fumigant]] for treatment of logs for [[termite]]s and [[beetle]]s, control of [[moth]]s in [[beehive (beekeeping)|beehives]], and as a preparation for [[dye]]s and [[wax]]es. yes ==Health effects== The [[Health effects|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.<ref> {{cite web|url=http://www.atsdr.cdc.gov/tfacts37.html |title=ToxFAQs for 1,2-Dibromoethane |accessdate=2007-02-20 }}</ref> [[Red]]ness and [[inflammation]], including [[skin]] [[blister]]s and [[mouth]] and [[stomach]] [[ulcer]]s, can occur if large amounts are swallowed. One accidental swallowing caused death in a woman. It is highly unlikely that there would be a risk of death to people from low-level exposure. Although very little is known about the effects from breathing 1,2-dibromoethane over a long period of time, some male workers had reproductive effects including damage to their sperm. In rats, death occurred from breathing high levels for a short time. Lower levels caused [[liver]] and [[kidney damage]]. When rats breathed air or ate food containing 1,2-dibromoethane for short or long periods of time, they were less fertile or had abnormal sperm. 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. 1,2-Dibromoethane is not known to cause [[birth defect]]s in humans.<ref> {{cite web|url=http://www.atsdr.cdc.gov/tfacts37.html |title=ToxFAQs for 1,2-Dibromoethane |accessdate=2007-02-20 }}</ref> ==References== <references/> ==External links== * [http://www.npi.gov.au/database/substance-info/profiles/31.html National Pollutant Inventory 1,2-Dibromoethane Fact Sheet] * [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] * [http://www.atsdr.cdc.gov/tfacts37.html ATSDR ToxFAQs] {{DEFAULTSORT:Dibromoethane, 1,2-}} [[Category:Insecticides]] [[Category:Organobromides]] [[Category:Fumigants]] [[Category:Flame retardants]] [[Category:Hazardous air pollutants]] [[Category:Fuel additives]] [[de:1,2-Dibromethan]] [[es:1,2-dibromoetano]] [[ja:1,2-ジブロモエタン]]