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Key Documents

V1902

Sigma-Aldrich

Vinyl bromide

98%

Synonym(s):

Bromoethylene

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About This Item

Linear Formula:
CH2=CHBr
CAS Number:
Molecular Weight:
106.95
Beilstein/REAXYS Number:
1361370
EC Number:
MDL number:
UNSPSC Code:
12162002
PubChem Substance ID:
NACRES:
NA.23

vapor density

3.8 (15 °C, vs air)

Quality Level

vapor pressure

1551 mmHg ( 37.8 °C)

assay

98%

autoignition temp.

986 °F

contains

200 ppm monomethyl ether hydroquinone as inhibitor

expl. lim.

15 %

bp

16 °C/750 mmHg (lit.)

mp

−139 °C (lit.)

density

1.517 g/mL at 25 °C (lit.)

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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Application

  • FTIR and Raman Spectroscopy Study of Soot Deposits: Investigates soot formation during the infrared multiphoton dissociation of vinyl bromide, suggesting potential applications in materials science regarding soot characteristics (Samoudi et al., 2022).
  • Nickel-Catalyzed Reductive Cross-Coupling: Describes a method for coupling vinyl bromides with unactivated alkyl halides, highlighting its utility in synthetic organic chemistry for creating complex molecules (Gong et al., 2017).
  • Silver-Promoted Synthesis of Vinyl Sulfones: This study explores the reactivity of vinyl bromides with sulfonyl hydrazides under aqueous conditions, applicable to pharmaceutical synthesis due to the biorelevance of sulfones (Zhang et al., 2020).
  • Visible Light on Vinyl Halides: Examines the photocatalytic properties of vinyl bromides, which could influence the development of green chemistry applications (Pagire et al., 2020).
  • Palladium Catalyzed Cross-Coupling of Diboronates: Focuses on the reactions of vinyl bromides with diboronates, offering insights into new methodologies for constructing biologically active compounds (Li et al., 2014).

Other Notes

V1902-100 g, V1902-900 g, and 1902-2.2 kg includes installed 316SS needle valve.

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Stainless steel hose adapter Z146838 or stainless steel body mini gas regulator Z513547 is recommended.

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Danger

Hazard Classifications

Acute Tox. 4 Oral - Carc. 1B - Flam. Gas 1A - Press. Gas Liquefied gas

Storage Class

2A - Gases

wgk_germany

WGK 3

flash_point_f

55.4 °F

flash_point_c

13 °C

ppe

Eyeshields, Faceshields, Gloves


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Changhui Sun et al.
Organic letters, 11(18), 4084-4087 (2009-08-20)
With the catalysis of CuI/trans-N,N'-dimethylcyclohexane-1,2-diamine, a number of carboxylic acids underwent efficient intramolecular O-vinylation with vinyl bromides leading to the synthesis of the corresponding five- and six-membered enol lactones. The same catalytic system also led to the efficient cycloisomerization of
Qiwu Zhao et al.
Organic letters, 10(18), 4037-4040 (2008-08-30)
A general and highly efficient synthesis of 4-alkylidene-2-azetidinones was achieved by the Cu(I)-catalyzed intramolecular C-N coupling of amides with vinyl bromides. This 4-exo ring closure was found to be fundamentally preferred over other modes (5-exo, 6-exo, and 6-endo) of cyclization
Carcinogenicity of 1,3-butadiene, ethylene oxide, vinyl chloride, vinyl fluoride, and vinyl bromide.
Yann Grosse et al.
The Lancet. Oncology, 8(8), 679-680 (2007-08-30)
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.
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

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