4-Bromo-4',4''-dimethyltriphenylamine
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4-Bromo-4',4''-dimethyltriphenylamine
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CAS No:
58047-42-0
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Formula:
C20H18BrN
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Chemical Name:
4-Bromo-4',4''-dimethyltriphenylamine
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Synonyms:
(4-Bromo-phenyl)-di-p-tolyl-amine;4-BROMO-4'',4''-DIMETHYLTRIPHENYLAMINE;4-BROMO-4'',4''-DIMETHYLTRIPHENYLAMINE,95.0+%(GC);4-Bromo-N,N-di-p-tolylaniline;4-Bromo-N,N-dip-tolylbenzenamine ,97%;4-broMo -4',4''- twoMethyl threeaniline;BDMTPA;4-Bromo-N,N-bis(4-methylphenyl)benzenamine
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CAS No:
Safety Information
NONH for all modes of transport
3
22-36/37/38
26
Xn
P261-P305 + P351 + P338
H302-H315-H319-H335
4-Bromo-4',4''-dimethyltriphenylamine Use and Manufacturing
To a solution of N, N’-ditolylaniline (10 g, 36.6 mmol) in dichloromethane (200 mE) was added n-bromosuccinimide (NES) (6.764 g, 38 mmol) at RT. The whole was stirred for about 3 hours. After filtering off the solid, the solution was loaded on silica gel, and purified by flash column (hexanes to hexanes dichloromethane 4:1). The desired fraction was collected and a white solid (Compound 25) was obtained afterremoval of solvents (12.86 g, in 99.7percent yield)Under a nitrogen atmosphere, n a 1 L three-necked flask equipped with a stirrer, 13.0 g (47.6 mmol) of the compound (B-3), 150 mL of dichloromethane was added, and the mixture was stirred at room temperature for 5 minutes. To this solution, 8.89 g (49.9 mmol) of N-bromosuccinimide, was dissolved in 200 mL of dichloromethane, was added dropwise over 1 hour. After completion of the dropwise addition, the mixture was further stirred at room temperature for 5 hours. After completion of the reaction, 150 mL of pure water pure water was added to the reaction solution, and the mixture was separated and separated. Further, after washing and separating with 150 mL of pure water, then saturated brine, the obtained organic layer was concentrated under reduced pressure, and the solvent was distilled off. The obtained residue was purified by silica gel column chromatography, by recrystallization from methanol, white crystals 12.9 g (yield 77percent, purity 99.9percent) was obtained.4, 4'-Dimethyltriphenylamine (5.6 g, 20.4 mmol) was dissolved in DMF (25 ml), and a solution of NBS (3.6 g, 20.4 mmol) in DMF (25 ml) was added dropwise. After completion of addition, the mixture was stirred at room temperature overnight. Water (100 ml) was added to the reaction solution, and the crude product was extracted with diethyl ether, dried with magnesium sulfate and concentrated under reduced pressure. The green oily residue was treated with methanol to crystallize to obtain 4-bromo-N, N-bis(4-methylphenyl)aniline (3) (4.9 g, 74percent). Ή NMR (600MHz, CDC1General procedure: General procedure for the palladium-catalyzed reaction General procedure: Intermediates 1-1 (5.0 g, 0.018 mol), 4-bromo-N, N-dip-tolylaniline (12.5 g, 0.036 mol), Pd(dba)A solution of CuI (6.7 mg, 0.035 mmol), NaOA solution of CuI (6.7 mg, 0.035 mmol), NaO
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4-Bromo-4',4''-dimethyltriphenylamine
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