| Revision as of 07:28, 9 June 2011 editPashihiko (talk | contribs)Extended confirmed users3,559 editsNo edit summary← Previous edit |
Latest revision as of 20:03, 22 December 2024 edit undoInnerstream (talk | contribs)Autopatrolled, Extended confirmed users4,070 editsmNo edit summary |
| (36 intermediate revisions by 26 users not shown) |
| Line 1: |
Line 1: |
|
{{chembox |
|
{{chembox |
|
|
| Verifiedfields = changed |
| ⚫ |
| verifiedrevid = 372106860 |
|
|
|
| Watchedfields = changed |
| ⚫ |
| ImageFile = Vinyl bromide.png |
|
|
⚫ |
| verifiedrevid = 433348913 |
|
⚫ |
| ImageFile = Vinyl bromide.svg |
|
| ImageSize = 120px |
|
| ImageSize = 120px |
|
| IUPACName = Bromoethene |
|
| PIN = Bromoethene |
|
| OtherNames = Vinyl bromide, 1-Bromoethene, Bromoethylene, 1-Bromoethylene, Monobromoethene, Monobromoethylene, R1140 B1, UN 1085 |
|
| OtherNames = Vinyl bromide<br />1-Bromoethene<br />Bromoethylene<br />1-Bromoethylene<br />Monobromoethene<br />Monobromoethylene |
|
| Section1 = {{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
| CASNo_Ref = {{cascite}} |
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo = 593-60-2 |
|
| CASNo = 593-60-2 |
|
| EINECS = 209-800-6 |
|
| ChEBI = 51311 |
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
| ⚫ |
| PubChem = 11641 |
|
|
| SMILES = C=CBr |
|
| UNII = 83NRW59KFY |
|
|
| EINECS = 209-800-6 |
| ⚫ |
| InChI = 1/C2H3Br/c1-2-3/h2H,1H2 |
|
| ⚫ |
| RTECS = KU8400000 |
|
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| KEGG_Ref = {{keggcite|correct|kegg}} |
|
| KEGG = C19184 |
|
| 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 |
|
|Section2={{Chembox Properties |
|
| Formula = C<sub>2</sub>H<sub>3</sub>Br |
|
| Formula = C<sub>2</sub>H<sub>3</sub>Br |
|
| MolarMass = 106.95 g/mol |
|
| MolarMass = 106.95 g/mol |
|
| Appearance = Colorless gas with pungent odor |
|
| Appearance = Colorless gas or liquid |
|
| Density = 1.525 g/cm<sup>3</sup> at boiling point (liquid) |
|
| Odor = pleasant<ref name=PGCH/> |
|
|
| Density = 1.525 g/cm<sup>3</sup> at boiling point (liquid) |
|
1.4933 g/cm<sup>3</sup> at 20 °C |
|
1.4933 g/cm<sup>3</sup> at 20 °C |
|
| MeltingPt = -137.8 °C |
|
| MeltingPtC = -137.8 |
|
| BoilingPt = 15.8 °C |
|
| BoilingPtC = 15.8 |
|
| Solubility = Insoluble |
|
| Solubility = Insoluble |
|
| LogP = 1.57 |
|
| LogP = 1.57 |
|
| VaporPressure = 206.8 kPa at 37.8 °C |
|
| VaporPressure = 206.8 kPa at 37.8 °C |
| ⚫ |
}} |
|
| ⚫ |
| Section3 = {{Chembox Hazards |
|
|
| MainHazards = Toxic ('''T'''), Highly flammable ('''F+''') |
|
| ⚫ |
| NFPA-H = 2 |
|
| ⚫ |
| NFPA-F = 4 |
|
| ⚫ |
| NFPA-R = 1 |
|
| ⚫ |
| NFPA-O = |
|
|
| RPhrases = {{R12}}, {{R20/21/22}}, {{R36/37/38}}, {{R45}} |
|
|
| SPhrases = {{S45}}, {{S53}} |
|
|
| FlashPt = 5 °C |
|
|
| Autoignition = 530 °C |
|
| ⚫ |
| ExploLimits = 6 - 15 % |
|
|
}} |
|
}} |
|
⚫ |
|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%<ref name=PGCH/> |
|
|
| PEL = none<ref name=PGCH>{{PGCH|0657}}</ref> |
|
|
| IDLH = N.D.<ref name=PGCH/> |
|
|
| REL = Ca<ref name=PGCH/> |
|
⚫ |
}} |
|
}} |
|
}} |
|
'''Vinyl bromide''' is a simple ]. It is soluble in ], ], ], ] and ]. |
|
'''Vinyl bromide''' is the organobromine compound with the formula {{chem2|CH2\dCHBr}}. Classified as a ], it is a colorless gas at room temperature. It is used as a ] and a ]. |
|
|
|
|
|
|
==Synthesis, reactions, and applications== |
|
== Uses == |
|
|
|
It is produced from ]: |
|
Vinyl bromide is used to manufacture bromopolymers and mainly ]. Further it is used as an ] agent. |
|
|
|
:{{chem2|CH2Br\sCH2Br -> CH2\dCHBr + HBr}} |
|
|
|
|
|
|
{{chem2|CH2\dCHBr}} is mainly consumted as a ] to confer ] properties to ]s.<ref name=Ullmann>{{ 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 }}</ref> |
| ⚫ |
== Safety precautions == |
|
|
Vinyl bromide is highly flammable liquid and reacts violently with ]s. |
|
|
|
|
|
|
|
Vinyl bromide reacts with magnesium to give the corresponding ] {{chem2|CH2\dCHMgBr}}.<ref>{{cite journal|title=Di-''n''-butyldivinyltin|author=Dietmar Seyferth|journal=Org. Synth. |year=1959|volume=39|page=10|doi=10.15227/orgsyn.039.0010}}</ref><ref>{{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 }}</ref> |
| ⚫ |
It is listed in ] as a suspected human ]. |
|
|
|
|
|
⚫ |
== Safety precautions == |
|
⚫ |
Vinyl bromide is listed in ] as a suspected human ]. |
|
|
|
|
|
== See also == |
|
== See also == |
| Line 55: |
Line 76: |
|
* ] |
|
* ] |
|
* ] |
|
* ] |
|
|
|
|
|
==References== |
|
|
{{Reflist}} |
|
|
|
|
|
== External links == |
|
== External links == |
| Line 60: |
Line 84: |
|
*{{PGCH|0657}} |
|
*{{PGCH|0657}} |
|
* |
|
* |
|
* |
|
* |
|
* |
|
* |
|
* |
|
* |
|
* |
|
* |
|
* |
|
* |
|
* |
|
* |
|
* |
|
* |
|
* |
|
* |
|
* |
|
* |
|
* |
|
* |
|
|
|
|
|
|
{{Authority control}} |
| ⚫ |
] |
|
|
|
|
| ⚫ |
] |
|
|
⚫ |
] |
|
⚫ |
] |
|
] |
|
] |
|
|
|
|
|
|
|
|
] |
|
|
|
{{alkene-stub}} |
|
] |
|
|
] |
|
|
] |
|