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B82200

Sigma-Aldrich

4-Bromotoluene

98%

Sinônimo(s):

1-Methyl-4-bromobenzene, 4-Bromo-1-methylbenzene, 4-Methyl-1-bromobenzene, 4-Methylbromobenzene, 4-Tolyl bromide, p-Bromo(methyl)benzene, p-Methylbromobenzene, p-Tolyl bromide

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About This Item

Fórmula linear:
CH3C6H4Br
Número CAS:
106-38-7
Peso molecular:
171.03
Beilstein:
1903636
Número CE:
203-391-8
Número MDL:
MFCD00000109
Código UNSPSC:
12352100
ID de substância PubChem:
24892060
NACRES:
NA.22

Nível de qualidade

200

Ensaio

98%

forma

solid

pb

184 °C (lit.)

pf

26-29 °C (lit.)

densidade

1.39 g/mL at 25 °C (lit.)

cadeia de caracteres SMILES

Cc1ccc(Br)cc1

InChI

1S/C7H7Br/c1-6-2-4-7(8)5-3-6/h2-5H,1H3

chave InChI

ZBTMRBYMKUEVEU-UHFFFAOYSA-N

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Descrição geral

4-Bromotoluene is a p-substituted aryl bromide. 4-Bromotoluene undergoes C-O coupling reaction with 2,4-dimethylphenol catalyzed by the CuI/K2CO3/phen system. Complexes [Cu(phen)(1-(2,4-dimethylphenoxy)-4-methylbenzene)]+, {H[Cu(phen)(2,4-dimethylphenoxy)]}+ and [Cu(2,4-dimethylphenoxy)2]- were reported as intermediates during the reaction by in situ electrospray ionization mass spectrometry (ESI-MS) analysis. Suzuki coupling reaction of 4-bromotoluene and non-fluorescent phenylboronic acid (PBA) in the presence of palladium (II) acetate as a catalyst has been studied. Palladium catalyzed C-N cross-coupling reaction of 4-bromotoluene with piperidine in a microstructured continuous reactor has been described. 4-Bromotoluene has been reported to undergo Heck reaction with styrene in the presence of in situ generated palladium complexes of phosphine-functionalized N-heterocyclic carbene ligands.

Aplicação

4-Bromotoluene was used in the synthesis of ketones by Cu/Pd-catalyzed decarboxylative cross-coupling reaction.

Pictogramas

Exclamation markEnvironment
GHS07,GHS09

Palavra indicadora

Warning

Frases de perigo

H332,H411

Classificações de perigo

Acute Tox. 4 Inhalation - Aquatic Chronic 2

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análise (COA)

Lot/Batch Number
STBK2551
STBJ9475
STBH8117
STBG1123V
STBD9245V

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1-Bromo-4-chlorobenzene 99%

Sigma-Aldrich

B60428

1-Bromo-4-chlorobenzene

1-Bromo-4-nitrobenzene 99%

Sigma-Aldrich

167150

1-Bromo-4-nitrobenzene

4-Bromobenzyl bromide 98%

Sigma-Aldrich

112186

4-Bromobenzyl bromide

Naoya Kishikawa et al.
Journal of chromatography. A, 1216(40), 6873-6876 (2009-09-01)
The fluorogenic derivatization method for aryl halide was developed for the first time. This method was based on the formation of fluorescent biphenyl structure by Suzuki coupling reaction between aryl halides and non-fluorescent phenylboronic acid (PBA). We measured the fluorescence
Hong-Jie Chen et al.
Dalton transactions (Cambridge, England : 2003), 43(29), 11410-11417 (2014-06-18)
The C-O coupling reaction between 2,4-dimethylphenol and 4-bromotoluene catalyzed by the CuI/K2CO3/phen system can be inhibited by the radical scavenger cumene. Complexes [Cu(i)(phen)(1-(2,4-dimethylphenoxy)-4-methylbenzene)](+) (denoted as A), {H[Cu(i)(phen)(2,4-dimethylphenoxy)]}(+) and [Cu(i)(2,4-dimethylphenoxy)2](-) (denoted as B) were observed by in situ electrospray ionization mass
Successful application of microstructured continuous reactor in the palladium catalysed aromatic amination.
Mauger C, et al.
Journal of Organometallic Chemistry, 690(16), 3627-3629 (2005)
Synthesis of ketones from alpha-oxocarboxylates and aryl bromides by Cu/Pd-catalyzed decarboxylative cross-coupling.
Lukas J Goossen et al.
Angewandte Chemie (International ed. in English), 47(16), 3043-3045 (2008-03-11)
Triaryl phosphine-functionalized N-heterocyclic carbene ligands for Heck reaction.
Wang A-E, et al.
Tetrahedron, 61(1), 259-266 (2005)
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Artigos

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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