157449
β-Bromostyrene
97%
Sinónimos:
beta-Bromostyrene, 1-Bromo-2-phenylethylene
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About This Item
Fórmula lineal:
C6H5CH=CHBr
Número de CAS:
Peso molecular:
183.05
Beilstein/REAXYS Number:
2038495
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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assay
97%
form
liquid
refractive index
n20/D 1.607 (lit.)
bp
110-112 °C/20 mmHg (lit.)
mp
7 °C (lit.)
density
1.427 g/mL at 25 °C (lit.)
functional group
bromo
phenyl
storage temp.
2-8°C
SMILES string
Br\C=C\c1ccccc1
InChI
1S/C8H7Br/c9-7-6-8-4-2-1-3-5-8/h1-7H/b7-6+
InChI key
YMOONIIMQBGTDU-VOTSOKGWSA-N
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General description
β-Bromostyrene is an α,β-unsaturated aromatic halide. It can be synthesized by catalytic Hunsdiecker reaction (CHR) of cinnamic acid. It is commonly utilized as a precursor for preparing substituted alkenes, corresponding acetylenes and also in the total synthesis of natural compounds and antibiotics.
Application
β-Bromostyrene was used in the one-pot method for the preparation of cinnamonitriles. It was also used in the preparation of pure ethyl Z- and E-α,α-difluoro-4-phenyl-3-butenoate and 1,3-diphenyl-1-butene. It may be used in the synthesis of β-tert-butylstyrene via cross coupling reaction with tert-butylmagnesium chloride in the presence of dichloro[1,1′-bis(diphenylphosphino)ferrocene]nickel(II) catalyst. It may also be used to prepare γ-but-2-enolactone by reacting with nickel carbonyl in the presence of alkynes.
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Journal of Organometallic Chemistry, 46(2), 375-377 (1972)
Catalytic Hunsdiecker Reaction and One-Pot Catalytic Hunsdiecker-Heck Strategy: Synthesis of α, β-Unsaturated Aromatic Halides, α-(Dihalomethyl) benzenemethanols, 5-Aryl-2, 4-pentadienoic acids, Dienoates and Dienamides.
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Hayashi T, et al.
Chemistry Letters (Jpn), 9(6), 767-768 (1980)
New method for the synthesis of β-bromostyrenes.
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Russian Chemical Bulletin, 50(8), 1401-1405 (2001)
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