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124141

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4-Bromostyrene

contains 0.05% 3,5-di-tert-butylcatechol as inhibitor, 97%

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Synonym(s):
1-(4-Bromophenyl)ethylene, 1-Bromo-4-ethenylbenzene, 1-Bromo-4-vinylbenzene, 4-Vinyl-1-bromobenzene, p -Bromostyrene
Linear Formula:
H2C=CHC6H4Br
CAS Number:
Molecular Weight:
183.05
Beilstein/REAXYS Number:
1634204
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.23

Quality Level

assay

97%

form

liquid

contains

0.05% 3,5-di-tert-butylcatechol as inhibitor

refractive index

n20/D 1.594 (lit.)

bp

89 °C/16 mmHg (lit.)

density

1.4 g/mL at 25 °C (lit.)

storage temp.

−20°C

SMILES string

Brc1ccc(C=C)cc1

InChI

1S/C8H7Br/c1-2-7-3-5-8(9)6-4-7/h2-6H,1H2

InChI key

WGGLDBIZIQMEGH-UHFFFAOYSA-N

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1 of 4

This Item
132675157449196525
vibrant-m

124141

4-Bromostyrene

vibrant-m

132675

3-Bromostyrene

vibrant-m

157449

β-Bromostyrene

vibrant-m

196525

4-Bromothioanisole

refractive index

n20/D 1.594 (lit.)

refractive index

n20/D 1.591 (lit.)

refractive index

n20/D 1.607 (lit.)

refractive index

-

density

1.4 g/mL at 25 °C (lit.)

density

1.406 g/mL at 25 °C (lit.)

density

1.427 g/mL at 25 °C (lit.)

density

-

bp

89 °C/16 mmHg (lit.)

bp

74-75 °C/3 mmHg (lit.)

bp

110-112 °C/20 mmHg (lit.)

bp

128-130 °C/10 mmHg (lit.)

contains

0.05% 3,5-di-tert-butylcatechol as inhibitor

contains

0.1% 3,5-di-tert-butylcatechol as inhibitor

contains

-

contains

-

form

liquid

form

liquid

form

liquid

form

-

General description

4-Bromostyrene is a para-halogenated styrene derivative. The proton spectra of 4-bromostyrene exhibits dipolar couplings consistent with planar ground state structures, only if the torsional motion of lowest frequency occurs at about 80cm-1. It undergoes Heck reaction with 2-bromo-6-methoxynaphthalene in the presence of sodium acetate and Hermann′s catalyst in N,N-dimethylacetamide to afford diarylethene.

Application

4-Bromostyrene was used in the following studies:
  • Structure activity relationships (SAR) study of the chemical and biochemical properties of the vinyl group of styrene.
  • Synthesis of silsesquioxanes (SQ) having 4-bromostyrenyl substituents.
  • To investigate the photochemical growth of Br-terminated self-assembled monolayers (SAMs) on Si(111).
  • Synthesis of poly(1,4-phenylenevinylene), via Heck reaction.
  • Synthesis of nitroolefins, via alkene cross-metathesis.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

167.0 °F - closed cup

flash_point_c

75 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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Synthesis of monomers and polymers by the Heck reaction.
Heitz W, et al.
Makromol. Chem., 189(1), 119-127 (1988)
Structural characterization of 4-bromostyrene self-assembled monolayers on Si (111).
Basu R, et al.
Langmuir, 23(4), 1905-1911 (2007)
Graham P Marsh et al.
Organic letters, 9(14), 2613-2616 (2007-06-07)
A synthesis of highly functionalized nitroalkenes is reported that utilizes a cross metathesis (CM) reaction between simple aliphatic nitro compounds and a range of substituted alkenes. This chemistry offers a simple and attractive route to nitroalkenes that would otherwise be
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