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
Quality Level
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
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
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
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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)
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
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