Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

157449

Sigma-Aldrich

β-Bromostyrene

97%

Synonym(s):

beta-Bromostyrene, 1-Bromo-2-phenylethylene

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Linear Formula:
C6H5CH=CHBr
CAS Number:
103-64-0
Molecular Weight:
183.05
Beilstein:
2038495
EC Number:
203-131-3
MDL number:
MFCD00000185
UNSPSC Code:
12352100
PubChem Substance ID:
24849679
NACRES:
NA.22

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

Looking for similar products? Visit Product Comparison Guide

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
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

215.6 °F - closed cup

Flash Point(C)

102 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 2

1 of 2

(1,2-Dibromoethyl)benzene ≥98%

Sigma-Aldrich

178012

(1,2-Dibromoethyl)benzene

1,4-Dibromobenzene 98%

Sigma-Aldrich

D39029

1,4-Dibromobenzene

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)
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)
New method for the synthesis of β-bromostyrenes.
Shastin AV, et al.
Russian Chemical Bulletin, 50(8), 1401-1405 (2001)
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)
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service