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Merck

B82200

4-Bromotoluene

98%

Sinónimos:

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 lineal:
CH3C6H4Br
Número CAS:
106-38-7
Peso molecular:
171.03
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24892060
EC Number:
203-391-8
Beilstein/REAXYS Number:
1903636
MDL number:
MFCD00000109

Nombre del producto

4-Bromotoluene, 98%

InChI key

ZBTMRBYMKUEVEU-UHFFFAOYSA-N

InChI

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

SMILES string

Cc1ccc(Br)cc1

assay

98%

form

solid

bp

184 °C (lit.)

mp

26-29 °C (lit.)

density

1.39 g/mL at 25 °C (lit.)

Quality Level

200

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Application

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

General description

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.

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

hcodes

H332,H411

Hazard Classifications

Acute Tox. 4 Inhalation - Aquatic Chronic 2

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
SDBB7038
STBL3488
STBK2551
STBJ9475
STBH8117

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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)
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)
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
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
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