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Sigma-Aldrich

4-Bromostyrene

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

Synonym(s):

1-(4-Bromophenyl)ethylene, 1-Bromo-4-ethenylbenzene, 1-Bromo-4-vinylbenzene, 4-Vinyl-1-bromobenzene, p -Bromostyrene

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About This Item

Linear Formula:
H2C=CHC6H4Br
CAS Number:
2039-82-9
Molecular Weight:
183.05
Beilstein:
1634204
EC Number:
218-022-6
MDL number:
MFCD00000110
UNSPSC Code:
12162002
PubChem Substance ID:
24847600
NACRES:
NA.23

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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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
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

167.0 °F - closed cup

Flash Point(C)

75 °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’.

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Synthesis and characterization of new hexahelicene derivatives.
Aloui F, et al.
Tetrahedron Letters, 48(11), 2017-2020 (2007)
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
Małgorzata Bołt et al.
Materials (Basel, Switzerland), 13(18) (2020-09-12)
Bifunctional silsesquioxanes create an attractive group of compounds with a wide range of potential applications, and recently they have gained much interest. They are known to be obtained mainly via hydrosilylation, but we disclose novel synthetic protocols based on different
View All Related Papers

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