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Merck

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:
Peso molecular:
106.95
Beilstein/REAXYS Number:
1361370
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.23

vapor pressure

12.46 psi ( 55 °C)
3.6 psi ( 20 °C)

Quality Level

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

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


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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)
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)
Qiwu Zhao et al.
The Journal of organic chemistry, 74(1), 459-462 (2008-11-27)
With CuI as the catalyst and K(3)PO(4) x 3 H(2)O as the base, highly efficient intramolecular S-vinylation of thiols with vinyl chlorides or bromides was successfully implemented without the help of an additional ligand. Moreover, the competition experiments revealed that
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

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