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Merck
CN

434191

Vinyl bromide solution

1.0 M in THF

Synonym(s):

Bromoethylene

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About This Item

Linear Formula:
CH2=CHBr
CAS Number:
Molecular Weight:
106.95
UNSPSC Code:
12162002
NACRES:
NA.23
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1361370
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InChI

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

SMILES string

BrC=C

InChI key

INLLPKCGLOXCIV-UHFFFAOYSA-N

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

Quality Level

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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.

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.

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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

Storage Class

3 - Flammable liquids

wgk

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

Regulatory Information

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Nickel/Copper Co-catalyzed Enantioselective Reductive Coupling of Oxabenzonorbornadienes with Vinyl Bromides
Yao Deng, et al.
advanced synthesis and catalysis, 365, 3265-3270 (2023)
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
Cheon-Gyu Cho et al.
Organic letters, 7(16), 3569-3572 (2005-07-29)
An effective, readily scalable two-step synthesis of trisubstituted (E)-vinyl bromides involving bromination of alpha,beta-unsaturated lactones followed by hydrolytic fragmentation has been developed. Several trisubstituted (E)-vinyl bromides, including multigram quantities of (+)-(E)-4-bromo-2-methyl-3-pentenol, a synthetic intermediate required for the C(8)-C(11) moieties of
Piotr Pawluć et al.
Organic letters, 11(15), 3390-3393 (2009-07-04)
A new, efficient protocol for the highly stereoselective one-pot synthesis of (E)-beta-aryl vinyl iodides and (E)-beta-aryl vinyl bromides from styrenes based on sequential ruthenium-catalyzed silylative coupling-N-halosuccinimide-mediated halodesilylation reactions is reported.
Hsin-Lun Kao et al.
Organic letters, 13(19), 5204-5207 (2011-09-02)
The synthesis of vinyl sulfides through the coupling reaction of thiols with vinyl iodides, bromides, and chlorides is described. The thiols can couple with aryl iodides in the presence of only 0.5 mol % Cu(2)O without the need for an

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