ChemicalBook CAS DataBase List N,N'-Diphenylbenzidine

N,N'-Diphenylbenzidine synthesis

14synthesis methods

Product Name:N,N'-Diphenylbenzidine
CAS Number:531-91-9
Molecular formula:C24H20N2
Molecular Weight:336.43

The synthesis of N,N'-Diphenylbenzidine is as follows:
3.12 g (10mmol) of 4,4'-dibromodiphenyl, 2.3 mL (25 mmol) of aniline, 2.9 g (30 mmol) of t-BuONa, 183 mg (0.2 mmol) of Pd2(dba)3, and 20 mg (0.1 mmol) of P(t-Bu)3 were dissolved in 30 mL of toluene, and then stirred at 90°C for 3 hrs. The reaction mixture was cooled to room temperature and three times extracted with distilled water and diethyl ether. Precipitates in an organic layer were filtered, washed with acetone and diethyl ether, and then dried in vacuum to obtain 0.3g of the intermediate compound C (yield: 90%). synthesis of N,N'-Diphenylbenzidine.png

92-86-4 Synthesis

92-86-4
386 suppliers
$15.00/25g

62-53-3 Synthesis

62-53-3
658 suppliers
$10.00/1g

531-91-9
347 suppliers
$7.00/1g

Yield:531-91-9 90%

Reaction Conditions:

with sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium⁽⁰⁾;tri-tert-butyl phosphine in toluene at 90; for 3 h;

Steps:

2

3.12 g (10mmol) of 4,4'-dibromodiphenyl, 2.3 mL (25 mmol) of aniline, 2.9 g (30 mmol) of t-BuONa, 183 mg (0.2 mmol) of Pd₂(dba)₃, and 20 mg (0.1 mmol) of P(t-Bu)₃ were dissolved in 30 mL of toluene, and then stirred at 90°C for 3 hrs. The reaction mixture was cooled to room temperature and three times extracted with distilled water and diethyl ether. Precipitates in an organic layer were filtered, washed with acetone and diethyl ether, and then dried in vacuum to obtain 0.3g of the intermediate compound C (yield: 90%). The structure of the intermediate compound C was identified with ¹H NMR. ¹H NMR (DMSO-d₆, 400MHz) δ (ppm) 8.22 (s, 2H), 7.48 (d,4H), 7.23 (t, 4H), 7.10 (dd, 8H), 6.82 (t, 2H); ¹³C NMR (DMSO-d₆, 100MHz) δ (ppm) 145.7, 144.3, 133.7, 131.4, 128.7, 121.2, 119.2, 118.9.

References:

EP1661888,2006,A1 Location in patent:Page/Page column 11-12

108-86-1 Synthesis