1,2-Dibromoethane

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1,2-Dibromoethane
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IUPAC name 1,2-dibromoethane
Other names ethylene dibromide
ethylene bromide
EDB
glycol bromide
ethylene bromide,
Bromofume (trade name),
Dowfume (trade name)
Identifiers
CAS number 106-93-4
RTECS number KH9275000
SMILES C(Br)CBr
Properties
Molecular formula C2H4Br2
Molar mass 187.86 g/mol
Appearance colorless liquid
Density 2.17 g/cm³, liquid
Melting point

9-10 °C (? K)

Boiling point

131-132 °C (? K)

Solubility in water 1 part in 250
Hazards
NFPA 704

NFPA 704.svg

0
3
0
 
R-phrases ,
S-phrases S53, S45, S61
Flash point >104 °C
Related Compounds
Related organobromides bromoethane
1,1-dibromoethane
Related compounds 1,2-dichloroethane
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

1,2-Dibromoethane is the chemical compound with the formula BrCH2CH2Br. 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:

CH2=CH2 + Br2 → BrCH2CH2Br

Uses

1,2-Dibromoethane is used in organic synthesis as an "entrainment reagent" to activate magnesium for certain Grignard reagents. In this process, the 1,2-dibromoethane is converted to ethylene and magnesium bromide, exposing a freshly etched portion of magnesium to the substrate.[1]

1,2-Dibromoethane is a precursor to many 1,2-disubstituted ethane derivatives, e.g. 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 termites and beetles, control of moths in beehives, and as a preparation for dyes and waxes.

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.[2]

Redness and inflammation, including skin blisters and mouth and stomach ulcers, 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 defects in humans.[3]

References

  1. 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.
  2. "ToxFAQs for 1,2-Dibromoethane". Retrieved 2007-02-20. 
  3. "ToxFAQs for 1,2-Dibromoethane". Retrieved 2007-02-20. 

External links


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