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124141

Sigma-Aldrich

4-Bromostyrene

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

Sinonimo/i:

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

Formula condensata:
H2C=CHC6H4Br
Numero CAS:
2039-82-9
Peso molecolare:
183.05
Beilstein:
1634204
Numero CE:
218-022-6
Numero MDL:
MFCD00000110
Codice UNSPSC:
12162002
ID PubChem:
24847600
NACRES:
NA.23

Saggio

97%

Stato

liquid

contiene

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

Indice di rifrazione

n20/D 1.594 (lit.)

P. ebollizione

89 °C/16 mmHg (lit.)

Densità

1.4 g/mL at 25 °C (lit.)

Temperatura di conservazione

−20°C

Stringa SMILE

Brc1ccc(C=C)cc1

InChI

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

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Categorie correlate

Descrizione generale

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.

Applicazioni

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.

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319

Classi di pericolo

Eye Irrit. 2 - Skin Irrit. 2

Codice della classe di stoccaggio

10 - Combustible liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

167.0 °F - closed cup

Punto d’infiammabilità (°C)

75 °C - closed cup

Dispositivi di protezione individuale

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificati d'analisi (COA)

Lot/Batch Number
BCCD3978
BCCC6609
BCCC0651
BCBW6435
BCBT6499

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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
Synthesis and characterization of new hexahelicene derivatives.
Aloui F, et al.
Tetrahedron Letters, 48(11), 2017-2020 (2007)
Structural characterization of 4-bromostyrene self-assembled monolayers on Si (111).
Basu R, et al.
Langmuir, 23(4), 1905-1911 (2007)
M Z Asuncion et al.
Journal of the American Chemical Society, 132(11), 3723-3736 (2010-03-02)
Polyphenylsilsesquioxane [PhSiO(1.5)](n) (PPS) and polyvinylsilsesquioxane [vinylSiO(1.5)](n) (PVS) are polymeric byproducts of the syntheses of the related T(8) octamers [PhSiO(1.5)](8) and [vinylSiO(1.5)](8). Here we demonstrate that random-structured PPS and PVS rearrange in the presence of catalytic amounts of Bu(4)N(+)F(-) in THF
Synthesis of monomers and polymers by the Heck reaction.
Heitz W, et al.
Makromol. Chem., 189(1), 119-127 (1988)
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Articoli

Heck Reaction

The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes and aryl or vinyl halides (or triflates) to afford substituted alkenes.

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