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Vinyl bromide

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(Redirected from Bromoethene)
Vinyl bromide
Names
Preferred IUPAC name Bromoethene
Other names Vinyl bromide
1-Bromoethene
Bromoethylene
1-Bromoethylene
Monobromoethene
Monobromoethylene
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.911 Edit this at Wikidata
EC Number
  • 209-800-6
KEGG
PubChem CID
RTECS number
  • KU8400000
UNII
UN number 1085
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H3Br/c1-2-3/h2H,1H2Key: INLLPKCGLOXCIV-UHFFFAOYSA-N
  • InChI=1/C2H3Br/c1-2-3/h2H,1H2Key: INLLPKCGLOXCIV-UHFFFAOYAI
SMILES
  • C=CBr
Properties
Chemical formula C2H3Br
Molar mass 106.95 g/mol
Appearance Colorless gas or liquid
Odor pleasant
Density 1.525 g/cm at boiling point (liquid)

1.4933 g/cm 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)
Solubility in water Insoluble
log P 1.57
Vapor pressure 206.8 kPa at 37.8 °C
Hazards
GHS labelling:
Pictograms GHS02: FlammableGHS08: Health hazard
Signal word Danger
Hazard statements H220, H350
Precautionary statements 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)
Autoignition
temperature 		530 °C (986 °F; 803 K)
Explosive limits 9%-15%
NIOSH (US health exposure limits):
PEL (Permissible) none
REL (Recommended) Ca
IDLH (Immediate danger) N.D.
Supplementary data page
Vinyl bromide (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

Synthesis, reactions, and applications

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.

Vinyl bromide reacts with magnesium to give the corresponding Grignard reagent CH2=CHMgBr.

Safety precautions

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

See also

References

  1. ^ 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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