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
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
Related Categories
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)
Qian Liao et al.
The Journal of organic chemistry, 74(16), 6371-6373 (2009-07-17)
A copper-catalyzed methodology for the coupling of vinyl bromides with azoles has been developed. This protocol uses a combination of 10 mol % of copper iodide and 20 mol % of ethylenediamine as catalyst. The reaction proceeds with various azoles
Yewen Fang et al.
Chemical communications (Cambridge, England), (28)(28), 3574-3576 (2005-07-13)
The first copper-catalyzed intramolecular O-vinylation of carbonyl compounds with vinyl bromides was reported, among which the efficient formation of 5-, 6- and even 7-membered cyclic alkenyl ethers was achieved with beta-ketoesters as nucleophiles.
Abha Chaudhary et al.
Molecular diversity, 16(2), 357-366 (2012-05-16)
A new series of benzocycloheptene amino vinyl bromide derivatives (9a-9m) were synthesized from isomeric mixture of himachalenes through two-step synthesis. The unusual structure of benzocycloheptene amino vinyl bromide derivative (9a) was confirmed by NMR and X-ray crystallography analyses. The newly
Bryden A F Le Bailly et al.
Chemical communications (Cambridge, England), 48(10), 1580-1582 (2011-11-02)
An iron-catalysed, hydride-mediated reductive cross-coupling reaction has been developed for the preparation of alkanes. Using a bench-stable iron(II) pre-catalyst, reductive cross-coupling of vinyl iodides, bromides and chlorides with aryl- and alkyl Grignard reagents successfully gave the products of formal sp(3)-sp(3)
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