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B82200

Sigma-Aldrich

4-Bromotoluene

98%

Synonym(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

Linear Formula:
CH3C6H4Br
CAS Number:
106-38-7
Molecular Weight:
171.03
Beilstein:
1903636
EC Number:
203-391-8
MDL number:
MFCD00000109
UNSPSC Code:
12352100
PubChem Substance ID:
24892060
NACRES:
NA.22

Quality Level

200

Assay

98%

form

solid

bp

184 °C (lit.)

mp

26-29 °C (lit.)

density

1.39 g/mL at 25 °C (lit.)

SMILES string

Cc1ccc(Br)cc1

InChI

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

InChI key

ZBTMRBYMKUEVEU-UHFFFAOYSA-N

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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.

Application

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

Pictograms

Exclamation markEnvironment
GHS07,GHS09

Signal Word

Warning

Hazard Statements

H332,H411

Hazard Classifications

Acute Tox. 4 Inhalation - Aquatic Chronic 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBK2551
STBJ9475
STBH8117
STBG1123V
STBD9245V

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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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Articles

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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