Bis(4-biphenylyl)amine synthesis
- Product Name:Bis(4-biphenylyl)amine
- CAS Number:102113-98-4
- Molecular formula:C24H19N
- Molecular Weight:321.41
Bis(4-bromophenyl)amine (4.0 g, 12.3 mmol) and phenylboronic acid (4.0 g, 32.7 mmol) were mixed in 250 mL of toluene and 60 mL of ethanol. The solution was bubbled with nitrogen while stirring for 15 minutes. Pd(PPh3)4 (1.4 g, 1.23 mmol) and K3PO4 (13.5 g, 64 mmol) were added in sequence. The mixture was heated to reflux overnight under nitrogen. After cooling, the reaction mixture was filtered through filter paper and the solvent was then evaporated. The solid was redissolved in nitrogen-purged hot toluene and was filtered through a Celite?/silica pad when the solution was still hot. The solvent was then evaporated. The white crystalline solid was washed by hexane and air dried to obtain 3.8 g of Bis(4-biphenylyl)amine.
Yield:102113-98-4 95%
Reaction Conditions:
with tri-tert-butyl phosphine;palladium diacetate;sodium t-butanolate in toluene at 110; for 12 h;
Steps:
8.1; 10.1; 11.1
(1) 4-bromobiphenyl (MW: 233.11) 23.31 g (0.1 mol), 4-aminobiphenyl (MW: 169.23) 17.77 g (0.105 mol), sodium tert-butoxide (MW: 96.10) 19.22 g ( 0.2mol), palladium(II) acetate (MW: 224.51) 0.22g, tri-tert-butylphosphorus (MW:202.32) 0.44g (0.0022mol) and toluene 336mL, put them in a 500mL reaction flask, insert a condenser, a thermometer, The reaction was stirred, heated to 110°C, and reacted for 12 hours; after the reaction was completed, the temperature was lowered, 140 mL of ethanol was added, filtered, washed with water, and dried to obtainBis([1,1’-biphenyl]-4-yl)amine(MW: 321.42) 30.53g (0.095mol), yield 95%;
References:
Yantai Xianhua Optoelectric Materials Institute Co., Ltd.;Sun Wei;Feng Peichuan;Chen Yue;Hu Lingfeng;Chen Yili;Wei Peng;Yang Yang CN111484468, 2020, A Location in patent:Paragraph 0092-0095; 0105-0109; 0113-0017
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