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Vinyl bromide

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 433348913

| ImageFile = Vinyl bromide.svg

| ImageSize = 120px

| PIN = Bromoethene

| OtherNames = Vinyl bromide
1-Bromoethene
Bromoethylene
1-Bromoethylene
Monobromoethene
Monobromoethylene

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 593-60-2

| ChEBI = 51311

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 83NRW59KFY

| EINECS = 209-800-6

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C19184

| PubChem = 11641

| RTECS = KU8400000

| UNNumber = 1085

| SMILES = C=CBr

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 11151

| InChIKey = INLLPKCGLOXCIV-UHFFFAOYAI

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C2H3Br/c1-2-3/h2H,1H2

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = INLLPKCGLOXCIV-UHFFFAOYSA-N

| InChI = 1/C2H3Br/c1-2-3/h2H,1H2

}}

|Section2={{Chembox Properties

| Formula = C2H3Br

| MolarMass = 106.95 g/mol

| Appearance = Colorless gas or liquid

| Odor = pleasant

| Density = 1.525 g/cm3 at boiling point (liquid)

1.4933 g/cm3 at 20 °C

| MeltingPtC = -137.8

| BoilingPtC = 15.8

| Solubility = Insoluble

| LogP = 1.57

| VaporPressure = 206.8 kPa at 37.8 °C

}}

|Section3={{Chembox Hazards

| NFPA-H = 2

| NFPA-F = 4

| NFPA-R = 1

| NFPA-S =

| GHSPictograms = {{GHS02}}{{GHS08}}

| GHSSignalWord = Danger

| HPhrases = {{H-phrases|220|350}}

| PPhrases = {{P-phrases|201|202|210|281|308+313|377|381|403|405|501}}

| FlashPtC = 5

| AutoignitionPtC = 530

| ExploLimits = 9%-15%

| PEL = none{{PGCH|0657}}

| IDLH = N.D.

| REL = Ca

}}

}}

Vinyl bromide is the organobromine compound with the formula {{chem2|CH2\dCHBr}}. 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:

:{{chem2|CH2Br\sCH2Br -> CH2\dCHBr + HBr}}

{{chem2|CH2\dCHBr}} is mainly consumted as a comonomer to confer fire retardant properties to acrylate polymers.{{ Ullmann | author = Dagani, M. J. | author2 = Barda, H. J. | author3 = Benya, T. J. | author4 = Sanders, D. C. | title = Bromine Compounds | doi = 10.1002/14356007.a04_405 }}

Vinyl bromide reacts with magnesium to give the corresponding Grignard reagent {{chem2|CH2\dCHMgBr}}.{{cite journal|title=Di-n-butyldivinyltin|author=Dietmar Seyferth|journal=Org. Synth. |year=1959|volume=39|page=10|doi=10.15227/orgsyn.039.0010}}{{cite journal |doi=10.15227/orgsyn.068.0116|title=Palladium-catalyzed Coupling of Vinyl Triflates with Organostannanes: 4-tert-butyl-1-vinylcyclohexene and 1-(4-tert-butylcyclohexen-1-yl)-2-propen-1-one |journal=Organic Syntheses |year=1990 |volume=68 |page=116|author=William J. Scott, G. T. Crisp, J. K. Stille }}

Safety precautions

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

See also

References

{{Reflist}}

External links

  • {{ICSC|0597|05}}
  • {{PGCH|0657}}
  • [http://ptcl.chem.ox.ac.uk/MSDS/VI/vinyl_bromide.html MSDS at Oxford University]
  • [https://web.archive.org/web/20071007185304/http://www.mathesontrigas.com/pdfs/msds/MAT24910.pdf MSDS at mathesontrigas.com]
  • [https://archive.today/20121213074702/http://www.epa.gov/iris/subst/0671.htm Vinyl bromide at IRIS]
  • [http://www.osha.gov/dts/sltc/methods/organic/org008/org008.html Vinyl bromide at osha.gov]
  • [http://www.inchem.org/documents/iarc/vol71/034-vinbrom.html IARC Summary & Evaluation of vinyl bromide]
  • [https://web.archive.org/web/20070120233708/http://ntp.niehs.nih.gov/ntp/newhomeroc/roc10/VB.pdf Report on Carcinogens Background Document for Vinyl Bromide]
  • [https://www.organic-chemistry.org/synthesis/C1Br/vinylbromides.shtm Synthesis of vinyl bromides]
  • [https://web.archive.org/web/20061009173240/http://www.cstl.nist.gov/div838/kinetics2001/agenda/f_session/f20/f20.htm The Kinetics of Pyrolysis of Vinyl Bromide]
  • [https://www.nist.gov/kinetics/spectra/bromoalkenes/UV%20Spectra%20-%20BromoAlkenes%201.PDF UV absorption spectra]
  • [https://www.nist.gov/kinetics/spectra/vinyl_4.gif UV Spectrum and Cross Sections]
  • [https://web.archive.org/web/20070927225153/http://www.muhlenberg.edu/depts/chemistry/chem201woh/1Hbromoethene.html 1H NMR spectrum]

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Category:Bromoalkenes

Category:Vinyl compounds

Category:IARC Group 2A carcinogens

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