|Jmol-3D images||Image 1|
|Molar mass||187.86 g mol−1|
|Density||2.18 g mL−1|
9-10 °C, 282.5-283.3 K, 49-50 °F
129-133 °C, 402-406 K, 264-271 °F
|Vapor pressure||1.56 kPa|
|kH||14 μmol Pa kg−1|
|Refractive index (nD)||1.539|
|Std enthalpy of
|−1.2419–−1.2387 MJ mol−1|
|223.30 J K−1 mol−1|
|Specific heat capacity, C||134.7 J K−1 mol−1|
|GHS signal word||DANGER|
|GHS hazard statements||H301, H311, H315, H319, H331, H335, H350, H411|
|GHS precautionary statements||P261, P273, P280, P301+310, P305+351+338|
|EU classification||T N|
|R-phrases||R45, R23/24/25, R36/37/38, R51/53|
|Flash point||>104 °C|
| (what is: / ?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
1,2-Dibromoethane, also known as ethylene dibromide (EDB), is the organobromine compound with the chemical formula (CH2Br)2. Although trace amounts occur naturally in the ocean, where it is formed probably by algae and kelp, it is mainly synthetic. It is a colorless liquid with a sweet odor, detectable at 10 ppm, is a widely used and sometimes-controversial fumigant.
Preparation and use
- CH2=CH2 + Br2 → BrCH2CH2Br
Historically, 1,2-dibromoethane was used as an anti-knock additive in leaded fuels. It reacts with lead residues to generate volatile lead bromides, thereby preventing fouling of the engine.
It has been used as a pesticide in soil and on various crops. The applications were initiated after the forced retirement of 1,2-dibromo-3-chloropropane (DBCP). Most of these uses have been stopped in the U.S. It continues to be used as a fumigant for treatment of logs for termites and beetles, for control of moths in beehives.
In the laboratory, 1,2-dibromoethane is used in organic synthesis as a source of bromine, e.g., to brominate carbanions and to activate magnesium for certain Grignard reagents. In the latter process, the 1,2-dibromoethane is converted to ethylene and magnesium bromide, exposing a freshly etched portion of magnesium to the substrate.
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. 1,2-Dibromoethane is not known to cause birth defects in humans. Swallowing has caused death at 40 mL doses
- "Ethylene Dibromide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification. Retrieved 19 June 2012.
- Dagani, M. J.; Barda, H. J.; Benya, T. J.; Sanders, D. C. (2005), "Bromine Compounds", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a04_405
- Seyferth, D. (2003). "The Rise and Fall of Tetraethyllead. 2". Organometallics 22 (25): 5154–5178. doi:10.1021/om030621b.
- "Toxicological Profile for 1,2-Dibromoethane". Archived from the original on 2009-11-22. Retrieved 2009-11-22.
- Maynard, G. D. (2004). "1,2-Dibromoethane". In L. Paquette. Encyclopedia of Reagents for Organic Synthesis. New York: J. Wiley & Sons. doi:10.1002/047084289.
- "Ranking Possible Cancer Hazards on the HERP Index". Retrieved 2010-10-14.
- National Pollutant Inventory 1,2-Dibromoethane Fact Sheet
- Congressional Research Service (CRS) Reports regarding Ethylene Dibromide
- ATSDR ToxFAQs
- CDC - NIOSH Pocket Guide to Chemical Hazards