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434191

Sigma-Aldrich

Vinyl bromide solution

1.0 M in THF

Sinónimos:

Bromoethylene

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About This Item

Fórmula lineal:
CH2=CHBr
Número de CAS:
593-60-2
Peso molecular:
106.95
Beilstein/REAXYS Number:
1361370
MDL number:
MFCD00000183
UNSPSC Code:
12162002
PubChem Substance ID:
24867180
NACRES:
NA.23

vapor pressure

12.46 psi ( 55 °C)
3.6 psi ( 20 °C)

form

liquid

concentration

1.0 M in THF

density

0.927 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

BrC=C

InChI

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

InChI key

INLLPKCGLOXCIV-UHFFFAOYSA-N

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General description

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.

signalword

Danger

Hazard Classifications

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

target_organs

Central nervous system, Respiratory system

supp_hazards

EUH019

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

1.4 °F - closed cup

flash_point_c

-17 °C - closed cup

ppe

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

Certificados de análisis (COA)

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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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