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B82200

Sigma-Aldrich

4-Bromotoluene

98%

Sinonimo/i:

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

Formula condensata:
CH3C6H4Br
Numero CAS:
106-38-7
Peso molecolare:
171.03
Beilstein:
1903636
Numero CE:
203-391-8
Numero MDL:
MFCD00000109
Codice UNSPSC:
12352100
ID PubChem:
24892060
NACRES:
NA.22

Livello qualitativo

200

Saggio

98%

Forma fisica

solid

P. eboll.

184 °C (lit.)

Punto di fusione

26-29 °C (lit.)

Densità

1.39 g/mL at 25 °C (lit.)

Stringa SMILE

Cc1ccc(Br)cc1

InChI

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

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Categorie correlate

Descrizione generale

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.

Applicazioni

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

Pittogrammi

Exclamation markEnvironment
GHS07,GHS09

Avvertenze

Warning

Indicazioni di pericolo

H332,H411

Classi di pericolo

Acute Tox. 4 Inhalation - Aquatic Chronic 2

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
STBK2551
STBJ9475
STBH8117
STBG1123V
STBD9245V

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3-Bromo[1,1′-biphenyl]-4-ol AldrichCPR

Sigma-Aldrich

OTV000161

3-Bromo[1,1′-biphenyl]-4-ol

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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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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