B82200

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
• 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

Properties

• 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

Description

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.

Safety Information

• Pictograms: GHS07,GHS09
• Signal Word: Warning
• Hazard Statements: H332,H411
• Precautionary Statements: P261 - P271 - P273 - P304 + P340 + P312 - P391 - P501
• 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