1,2-Dibromoethane

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Skeletal formula of 1,2-dibromoethane with all explicit hydrogens added 1,2-Dibromoethane Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) The Royal Society of Chemistry 2014 Cambridge 657 10.1039/9781849733069-FP001 978-0-85404-182-4 Front Matter Ethylene dibromide Ethylene bromide Glycol bromide Di(bromomethyl) EDBJune 2012 106-93-4 correct CAS changed FDA 1N41638RNO 7839 7551 correct chemspider 203-444-5 1605 C11088 correct kegg Ethylene+Dibromide 28534 correct EBI 452370 correct EBI KH9275000 605266 BrCCBr 1S/C2H4Br2/c3-1-2-4/h1-2H2 correct chemspider PAAZPARNPHGIKF-UHFFFAOYSA-N correct chemspider 2 4 2 Colorless liquid faintly sweet 2.18 g mL−1 282.5 to 283.3 402 to 406 2.024 1.56 kPa 14 μmol Pa kg−1 1.539 0.4% (20 °C) −1.2419–−1.2387 MJ mol−1 223.30 J K−1 mol−1 134.7 J K−1 mol−1 skull and crossbones health hazard environment DANGER 301 311 315 319 331 335 350 411 261 273 280 301+310 305+351+338 3 0 0 104 55.0 mg kg−1 (oral, rabbit) 79.0 mg kg−1 (oral, chicken) 110.0 mg kg−1 (oral, guinea pig) 130.0 mg kg−1 (oral, quail) 300.0 mg kg−1 (dermal, rabbit) TWA 20 ppm C 30 ppm 50 ppm [5-minute maximum peak]0270 Ca [100 ppm] carcinogen Ca TWA 0.045 ppm C 0.13 ppm [15-minute] 1831 ppm (rat, 30 min)691 ppm (rat, 1 hr)106934 Ethylene dibromide 200 ppm (rat, 8 hr)400 ppm (guinea pig, 3 hr) alkanes Dibromomethane Bromoform Tetrabromomethane 1,1-Dibromoethane Tetrabromoethane 1,2-Dibromopropane 1,3-Dibromopropane 1,2,3-Tribromopropane 1,2-Dibromoethane, also known as ethylene dibromide (EDB), is an organobromine compound with the chemical formula C 2 H 4 Br 2. Although trace amounts occur naturally in the ocean, where it is probably formed by algae and kelp, 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 fumigant. The combustion of 1,2-dibromoethane produces hydrogen bromide gas that is significantly corrosive.https://www.sigmaaldrich.com Safety Data Sheet for CAS-No.:106-93-4 Ethylene dibromide Preparation and use It is produced by the reaction of ethylene gas with bromine,2017 Preparation and purification of 1,2-dibromoethane https://www.thieme-connect.de/media/synlett/201713/supmat/sup_st-2017-b0194-l_10-1055_s-0036-1588180.pdf Synlett 28 49–51 in a classic halogen addition reaction: CH2=CH2 + Br2 → BrCH2–CH2Br Historically, 1,2-dibromoethane was used as a component in anti-knock additives in leaded fuels. It reacts with lead residues to generate volatile lead bromides, thereby preventing fouling of the engine with lead deposits. Seyferth, D. The Rise and Fall of Tetraethyllead. 2 Organometallics 2003 22 25 5154–5178 10.1021/om030621b Pesticide 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). 10.1002/14356007.a04_405.pub2 Bromine Compounds Ullmann's Encyclopedia of Industrial Chemistry 2013 Yoffe David Frim Ron Ukeles Shmuel D. Dagani Michael J. Barda Henry J. Benya Theodore J. Sanders David C. 1–31 978-3-527-30385-4 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, and for control of moths in beehives. http://www.atsdr.cdc.gov/toxprofiles/tp37.pdf Toxicological Profile for 1,2-Dibromoethane 2009-11-22 https://web.archive.org/web/20091122182238/http://www.atsdr.cdc.gov/toxprofiles/tp37.pdf 2009-11-22 Reagent 1,2-Dibromoethane has wider applications in the preparation of other organic compounds including those carrying modified diazocine ringsHamada, Y. Mukai. S. 1996 Synthesis of ethano-Tröger's base, configurationally stable substitute of Tröger's base Tetrahedron Asymmetry 7 9 2671–2674 10.1016/0957-4166(96)00343-6 and vinyl bromide that is a precursor to some fire retardants. In organic synthesis, 1,2-dibromoethane is used to brominate carbanions and to activate magnesium for certain Grignard reagents. In the latter process, 1,2-dibromoethane reacts with magnesium, producing ethylene and magnesium bromide, which are innocuous, exposing a more active portion of the magnesium particle to the substrate. Maynard, G. D. 1,2-Dibromoethane Encyclopedia of Reagents for Organic Synthesis Paquette, L. 2004 J. Wiley & Sons New York 10.1002/047084289X.rd039 0471936235 Health effects 1,2-Dibromoethane causes changes in the metabolism and severe destruction of living tissues. The known empirical LD50 values for 1,2-dibromoethane are 140 mg kg−1 (oral, rat), and 300.0 mg kg−1 (dermal, rabbit). 1,2-Dibromoethane is a known carcinogen, with pre-1977 exposure levels ranking it as the most carcinogenic substance on the HERP Index.https://www.nlm.nih.gov/toxnet/index.html https://web.archive.org/web/20190629174358/https://toxnet.nlm.nih.gov/cpdb/pdfs/herp.pdf 2019-06-29 live Ranking Possible Cancer Hazards from Rodent Carcinogens 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.https://www.atsdr.cdc.gov/mmg/mmg.asp?id=1062&tid=131 Toxic Substances Portal – 1,2-Dibromoethane 2019-09-28 2020-12-29 https://web.archive.org/web/20201229023525/https://www.atsdr.cdc.gov/MMG/MMG.asp?id=1062&tid=131 dead 1,2-Dibromoethane is not known to cause birth defects in humans. Swallowing has caused death from ingesting a 4.5 mL dose. References External links 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 Category:Endocrine disruptors Category:Insecticides Category:Bromoalkanes Category:Fumigants Category:Flame retardants Category:Fuel additives Category:IARC Group 2A carcinogens Category:Sweet-smelling chemicals Category:Haloethanes