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157449

Sigma-Aldrich

β-Bromostyrene

97%

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Synonym(s):
beta-Bromostyrene, 1-Bromo-2-phenylethylene
Linear Formula:
C6H5CH=CHBr
CAS Number:
Molecular Weight:
183.05
Beilstein/REAXYS Number:
2038495
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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.)

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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1 of 4

This Item
124141132683C4767
vibrant-m

157449

β-Bromostyrene

vibrant-m

124141

4-Bromostyrene

vibrant-m

132683

2-Bromostyrene

vibrant-m

C4767

β-Cyclodextrin

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

-

mp

7 °C (lit.)

mp

-

mp

-

mp

290-300 °C (dec.) (lit.)

form

liquid

form

liquid

form

liquid

form

powder

bp

110-112 °C/20 mmHg (lit.)

bp

89 °C/16 mmHg (lit.)

bp

102-104 °C/22 mmHg (lit.)

bp

-

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.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

215.6 °F - closed cup

flash_point_c

102 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Cross-Coupling of Tertiary Alkyl Grignard Reagents with β-Bromostyrene Catalyzed by Dichloro[1,1'-bis(diphenylphosphino)ferrocene]nickel (II).
Hayashi T, et al.
Chemistry Letters (Jpn), 9(6), 767-768 (1980)
Enantioselective Preparation of C2-Symmetrical Ferrocenyl Ligands for Asymmetric Catalysis.
Schwink L and Knochel P.
Chemistry (Weinheim An Der Bergstrasse, Germany), 4(5), 950-968 (1998)
The reaction of ?-bromostyrene with nickel carbonyl in the presence of alkynes.
Ryang M, et al.
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.
Naskar D and Roy S.
Tetrahedron, 56(10), 1369-1377 (2000)
New method for the synthesis of β-bromostyrenes.
Shastin AV, et al.
Russian Chemical Bulletin, 50(8), 1401-1405 (2001)

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