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434191

Sigma-Aldrich

Vinyl bromide solution

1.0 M in THF

Synonyme(s) :

Bromoethylene

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About This Item

Formule linéaire :
CH2=CHBr
Numéro CAS:
593-60-2
Poids moléculaire :
106.95
Numéro Beilstein :
1361370
Numéro MDL:
MFCD00000183
Code UNSPSC :
12162002
ID de substance PubChem :
24867180
Nomenclature NACRES :
NA.23

Pression de vapeur

12.46 psi ( 55 °C)
3.6 psi ( 20 °C)

Forme

liquid

Concentration

1.0 M in THF

Densité

0.927 g/mL at 25 °C

Température de stockage

2-8°C

Chaîne SMILES 

BrC=C

InChI

1S/C2H3Br/c1-2-3/h2H,1H2

Clé InChI

INLLPKCGLOXCIV-UHFFFAOYSA-N

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Catégories apparentées

Description générale

Vinyl bromide solution belongs to haloalkenes andis highly reactive due to the presence of an unsaturated vinyl group. It can provide flame retardancy to polymers or materials when incorporated into their structure. It is also a versatile building block for polymerization, addition reactions, substitution reactions, and cross-coupling reactions like Suzuki-Miyaura and Negishi reactions. It can be used to introduce radiolabel into molecules for medical imaging.

Application


  • Sequential Vinyl Radical Cyclization/Fixation of Carbon Dioxide through Electrochemical Reduction of Vinyl Bromide in the Presence of an Electron-Transfer Mediator: This study explores the electrochemical reduction of vinyl bromide with a focus on vinyl radical cyclization and carbon dioxide fixation (A Katayama, H Senboku, 2016).

  • A Comparison of the Wavelength-Dependent Photochemical Reactions of Ozone with Vinyl Bromide and Fluoride in Argon Matrices: The study compares the photochemical reactions of vinyl bromide and fluoride with ozone, examining their behavior in argon matrices (BS Ault, 2021).

Vinyl bromide solution can be used as a precursor for stereoselective synthesis of chiral 2-vinyl-tetrahydronaphthalens via asymmetric reductive coupling. These chiral compounds are valuable building blocks for natural products, agrochemicals, and liquid crystals.

Pictogrammes

FlameHealth hazardExclamation mark
GHS02,GHS08,GHS07

Mention d'avertissement

Danger

Classification des risques

Acute Tox. 4 Oral - Carc. 1B - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

Organes cibles

Central nervous system, Respiratory system

Risques supp

EUH019

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

1.4 °F - closed cup

Point d'éclair (°C)

-17 °C - closed cup

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Changhui Sun et al.
Organic letters, 11(18), 4084-4087 (2009-08-20)
With the catalysis of CuI/trans-N,N'-dimethylcyclohexane-1,2-diamine, a number of carboxylic acids underwent efficient intramolecular O-vinylation with vinyl bromides leading to the synthesis of the corresponding five- and six-membered enol lactones. The same catalytic system also led to the efficient cycloisomerization of
Qiwu Zhao et al.
Organic letters, 10(18), 4037-4040 (2008-08-30)
A general and highly efficient synthesis of 4-alkylidene-2-azetidinones was achieved by the Cu(I)-catalyzed intramolecular C-N coupling of amides with vinyl bromides. This 4-exo ring closure was found to be fundamentally preferred over other modes (5-exo, 6-exo, and 6-endo) of cyclization
Derek R Boyd et al.
Organic & biomolecular chemistry, 5(3), 514-522 (2007-01-26)
Enantiopure trans-dihydrodiols have been obtained by a chemoenzymatic synthesis from the corresponding cis-dihydrodiol metabolites, obtained by dioxygenase-catalysed arene cis-dihydroxylation at the 2,3-bond of monosubstituted benzene substrates. This generally applicable, seven-step synthetic route to trans-dihydrodiols involves a regioselective hydrogenation and a
Ian Paterson et al.
Organic letters, 12(16), 3724-3727 (2010-08-14)
Using a combination of asymmetric vinylogous Mukaiyama aldol and Stille cross-coupling reactions, an advanced polyene fragment of the chivosazoles was prepared in a highly stereocontrolled manner. This key C1-C13 pentaene subunit, featuring the conjugated (2E,4Z,6E,8Z)-tetraenoate motif and anti-configured C10 and
Carcinogenicity of 1,3-butadiene, ethylene oxide, vinyl chloride, vinyl fluoride, and vinyl bromide.
Yann Grosse et al.
The Lancet. Oncology, 8(8), 679-680 (2007-08-30)
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