Wikipedia

Vinyl bromide

Vinyl bromide is the organobromine compound with the formula CH2=CHBr. Classified as a vinyl halide, it is a colorless gas at room temperature. It is used as a reagent and a comonomer.

Vinyl bromide
Names
Preferred IUPAC name
Bromoethene
Other names
Vinyl bromide
1-Bromoethene
Bromoethylene
1-Bromoethylene
Monobromoethene
Monobromoethylene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.911 Edit this at Wikidata
EC Number
  • 209-800-6
KEGG
RTECS number
  • KU8400000
UNII
UN number 1085
  • InChI=1S/C2H3Br/c1-2-3/h2H,1H2 checkY
    Key: INLLPKCGLOXCIV-UHFFFAOYSA-N checkY
  • InChI=1/C2H3Br/c1-2-3/h2H,1H2
    Key: INLLPKCGLOXCIV-UHFFFAOYAI
  • C=CBr
Properties
C2H3Br
Molar mass 106.95 g/mol
Appearance Colorless gas or liquid
Odor pleasant[1]
Density 1.525 g/cm3 at boiling point (liquid)

1.4933 g/cm3 at 20 °C

Melting point −137.8 °C (−216.0 °F; 135.3 K)
Boiling point 15.8 °C (60.4 °F; 288.9 K)
Insoluble
log P 1.57
Vapor pressure 206.8 kPa at 37.8 °C
Hazards
GHS labelling:
GHS02: FlammableGHS08: Health hazard
Danger
H220, H350
P201, P202, P210, P281, P308+P313, P377, P381, P403, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 4: Will rapidly or completely vaporize at normal atmospheric pressure and temperature, or is readily dispersed in air and will burn readily. Flash point below 23 °C (73 °F). E.g. propaneInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
4
1
Flash point 5 °C (41 °F; 278 K)
530 °C (986 °F; 803 K)
Explosive limits 9%-15%[1]
NIOSH (US health exposure limits):
PEL (Permissible)
 none[1]
REL (Recommended)
 Ca[1]
IDLH (Immediate danger)
 N.D.[1]
Supplementary data page
Vinyl bromide (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis, reactions, and applications

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It is produced from ethylene dibromide:

CH2Br−CH2Br → CH2=CHBr + HBr

CH2=CHBr is mainly consumted as a comonomer to confer fire retardant properties to acrylate polymers.[2]

Vinyl bromide reacts with magnesium to give the corresponding Grignard reagent CH2=CHMgBr.[3][4]

Safety precautions

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Vinyl bromide is listed in List of IARC Group 2A carcinogens as a suspected human carcinogen.

See also

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References

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  1. ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0657". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ Dagani, M. J.; Barda, H. J.; Benya, T. J.; Sanders, D. C. "Bromine Compounds". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a04_405. ISBN 978-3527306732.
  3. ^ Dietmar Seyferth (1959). "Di-n-butyldivinyltin". Org. Synth. 39: 10. doi:10.15227/orgsyn.039.0010.
  4. ^ William J. Scott, G. T. Crisp, J. K. Stille (1990). "Palladium-catalyzed Coupling of Vinyl Triflates with Organostannanes: 4-tert-butyl-1-vinylcyclohexene and 1-(4-tert-butylcyclohexen-1-yl)-2-propen-1-one". Organic Syntheses. 68: 116. doi:10.15227/orgsyn.068.0116.{{cite journal}}: CS1 maint: multiple names: authors list (link)
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