World Library  
Flag as Inappropriate
Email this Article

1,2-Dibromoethane

Article Id: WHEBN0000241806
Reproduction Date:

Title: 1,2-Dibromoethane  
Author: World Heritage Encyclopedia
Language: English
Subject: Tetraethyllead, Bromine, Maui, EDB, Flame retardants
Collection: Bromoalkanes, Endocrine Disruptors, Flame Retardants, Fuel Additives, Fumigants, Hazardous Air Pollutants, Iarc Group 2A Carcinogens, Insecticides, Organobromides
Publisher: World Heritage Encyclopedia
Publication
Date:
 

1,2-Dibromoethane

1,2-Dibromoethane
Skeletal formula of 1,2-dibromoethane
Skeletal formula of 1,2-dibromoethane with all explicit hydrogens added
Spacefill model of 1,2-dibromoethane
Names
IUPAC name
1,2-Dibromoethane[1]
Other names
  • Ethylene bromide[2]
  • Ethylene dibromide[2]
  • Glycol bromide[2]
Identifiers
 Y
Abbreviations EDB
605266
ChEBI  Y
ChEMBL  Y
ChemSpider  Y
EC number 203-444-5
Jmol-3D images Image
KEGG  Y
MeSH
PubChem
RTECS number KH9275000
UN number 1605
Properties
C2H4Br2
Molar mass 187.86 g·mol−1
Appearance Colorless liquid
Odor sweet[2]
Density 2.18 g mL−1
Melting point 9.4 to 10.2 °C; 48.8 to 50.3 °F; 282.5 to 283.3 K
Boiling point 129 to 133 °C; 264 to 271 °F; 402 to 406 K
0.4% (20 °C)[2]
log P 2.024
Vapor pressure 1.56 kPa
14 μmol Pa kg−1
1.539
Thermochemistry
134.7 J K−1 mol−1
223.30 J K−1 mol−1
−1.2419–−1.2387 MJ mol−1
Hazards
Main hazards carcinogen[2]
GHS pictograms The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS) The environment pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H301, H311, H315, H319, H331, H335, H350, H411
P261, P273, P280, P301+310, P305+351+338
Toxic T Dangerous for the Environment (Nature) N
R-phrases R51/53
S-phrases S45
NFPA 704
0
3
0
Flash point > 104 °C (219 °F; 377 K)
Lethal dose or concentration (LD, LC):
LD50 (Median dose)
  • 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)
1831 ppm (rat, 30 min)
691 ppm (rat, 1 hr)[3]
200 ppm (rat, 8 hr)
400 ppm (guinea pig, 3 hr)[3]
US health exposure limits (NIOSH):
PEL (Permissible)
TWA 20 ppm C 30 ppm 50 ppm [5-minute maximum peak][2]
REL (Recommended)
Ca TWA 0.045 ppm C 0.13 ppm [15-minute][2]
Ca [100 ppm][2]
Related compounds
Related alkanes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N  (: Y/N?)

1,2-Dibromoethane, also known as ethylene dibromide (EDB), is 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.[4]

Contents

  • Preparation and use 1
    • Pesticide 1.1
    • Reagent 1.2
  • Health effects 2
  • References 3
  • External links 4

Preparation and use

It is produced by the reaction of ethylene with bromine, in a classic halogen addition reaction:

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.[5]

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).[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, for control of moths in beehives.[6]

Reagent

Ethylene bromide has wider applications in the preparation of other organic compounds. It is used to make vinyl bromide, a precursor to some fire retardants.[4]

In the laboratory, 1,2-dibromoethane is used in 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.[7]

Health effects

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.[8] Swallowing has caused death at 40 mL doses[6]

It is a known carcinogen, with pre-1977 exposure levels ranking it as the most carcinogenic substance on the HERP Index.[9]

References

  1. ^ "Ethylene Dibromide - Compound Summary". PubChem Compound. USA: National Center for Biotechnology Information. 16 September 2004. Identification. Retrieved 19 June 2012. 
  2. ^ a b c d e f g h i "NIOSH Pocket Guide to Chemical Hazards #0270".  
  3. ^ a b "Ethylene dibromide". Immediately Dangerous to Life and Health.  
  4. ^ a b c Dagani, M. J.; Barda, H. J.; Benya, T. J.; Sanders, D. C. (2005), "Bromine Compounds",  
  5. ^ Seyferth, D. (2003). "The Rise and Fall of Tetraethyllead. 2".  
  6. ^ a b "Toxicological Profile for 1,2-Dibromoethane" (PDF). Archived from the original (PDF) on 2009-11-22. Retrieved 2009-11-22. 
  7. ^ Maynard, G. D. (2004). "1,2-Dibromoethane". In L. Paquette. Encyclopedia of Reagents for Organic Synthesis. New York: J. Wiley & Sons.  
  8. ^ http://www.atsdr.cdc.gov/mmg/mmg.asp?id=1062&tid=131
  9. ^ "Ranking Possible Cancer Hazards on the HERP Index" (PDF). Retrieved 2010-10-14. 

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
This article was sourced from Creative Commons Attribution-ShareAlike License; additional terms may apply. World Heritage Encyclopedia content is assembled from numerous content providers, Open Access Publishing, and in compliance with The Fair Access to Science and Technology Research Act (FASTR), Wikimedia Foundation, Inc., Public Library of Science, The Encyclopedia of Life, Open Book Publishers (OBP), PubMed, U.S. National Library of Medicine, National Center for Biotechnology Information, U.S. National Library of Medicine, National Institutes of Health (NIH), U.S. Department of Health & Human Services, and USA.gov, which sources content from all federal, state, local, tribal, and territorial government publication portals (.gov, .mil, .edu). Funding for USA.gov and content contributors is made possible from the U.S. Congress, E-Government Act of 2002.
 
Crowd sourced content that is contributed to World Heritage Encyclopedia is peer reviewed and edited by our editorial staff to ensure quality scholarly research articles.
 
By using this site, you agree to the Terms of Use and Privacy Policy. World Heritage Encyclopedia™ is a registered trademark of the World Public Library Association, a non-profit organization.
 


Copyright © World Library Foundation. All rights reserved. eBooks from Project Gutenberg are sponsored by the World Library Foundation,
a 501c(4) Member's Support Non-Profit Organization, and is NOT affiliated with any governmental agency or department.