ChemicalBook CAS DataBase List N-PHENYL-3-BIPHENYLAMINE

N-PHENYL-3-BIPHENYLAMINE synthesis

8synthesis methods

Product Name:N-PHENYL-3-BIPHENYLAMINE
CAS Number:198275-79-5
Molecular formula:C18H15N
Molecular Weight:245.32

2113-57-7 Synthesis

2113-57-7
400 suppliers
$14.00/1g

62-53-3 Synthesis

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

198275-79-5
56 suppliers
$110.00/50mg

Yield: 95%

Reaction Conditions:

with 1,1'-bis-(diphenylphosphino)ferrocene;bis(dibenzylideneacetone)-palladium⁽⁰⁾;sodium t-butanolate in toluene for 2 h;Inert atmosphere;Reflux;

Steps:

1 2.1.1 Preparation of N-phenyl-[1,1'-biphenyl]-3-amine [13] (4)
General procedure: General procedure A. A dry, 250 mL nitrogen flushed flask was charged with aniline (2.09 g, 22.5 mmol), 3-bromo-1,1'-biphenyl (3.46 g, 15 mmol), sodium tert-butoxide (2.20 g, 22.5 mmol,), Pd(dba)₂ (0.35 g, 0.6 mmol), DPPF (0.34 g, 0.6 mmol), and toluene (50 mL). The reaction mixture was refluxed for 2 h. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (50 mL). The precipitate was filtered off and the filtrate was collected and evaporated. The crude product was purified by chromatography on silica gel with a mixture of hexane and dichloromethane (v/v = 1:1) to yield a white solid, 3.5 g, 95%. ¹H NMR (300 MHz, CDCl₃), δ 7.57 (d, J = 7.5 Hz, 2H), 7.42 (t, J = 7.2 Hz, 2H), 7.36-7.29 (m, 5H), 7.13 (t, J = 9.3 Hz, 3H), 7.06 (d, J = 9 Hz, 1H), 6.94 (t, J = 10 Hz, 1H), 5.78 (s, 1H). ¹³C NMR (75 MHz, CDCl₃), δ 143.6, 143.0, 142.5, 141.14, 129.7, 129.4, 128.7, 127.3, 127.1, 121.2, 119.9, 118.0, 116.6, 116.4.

References:

Huo, Shouquan;Harris, Caleb F.;Vezzu, Dileep A.K.;Gagnier, Joshua P.;Smith, Meredith E.;Pike, Robert D.;Li, Yumin [Polyhedron,2013,vol. 52,p. 1030 - 1040]