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434191

Sigma-Aldrich

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
Beilstein:
1361370
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
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.

Signal Word

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

Supplementary Hazards

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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.
James A Marshall et al.
Organic letters, 6(3), 445-448 (2004-01-30)
[reaction: see text] Additions of vinylic zinc bromide reagents to alpha-chiral aldehydes (R(1) = CH(2)OTBS, R(2) = Me; R(1) = Me, R(2) = OTBS) in the presence of lithiated (+)- or (-)-N-methylephedrine proceed with predominant reagent control to afford anti
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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