434191
Vinyl bromide solution
1.0 M in THF
Synonyme(s) :
Bromoethylene
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A propos de cet article
Formule linéaire :
CH2=CHBr
Numéro CAS:
Poids moléculaire :
106.95
UNSPSC Code:
12162002
NACRES:
NA.23
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1361370
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Laissez-nous vous aiderInChI
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
Catégories apparentées
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
Classe de stockage
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)
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
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
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)
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.
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