ChemicalBook CAS DataBase List 4,4'-biphenyldiacetonitrile

4,4'-biphenyldiacetonitrile synthesis

6synthesis methods

Product Name:4,4'-biphenyldiacetonitrile
CAS Number:7255-83-6
Molecular formula:C16H12N2
Molecular Weight:232.28

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Yield: 90%

Reaction Conditions:

with sodium cyanide in dimethyl sulfoxide at 20 - 49.84; for 44 h;

Steps:

1 Synthesis of the Intermediate 4,4’-bis(cyanomethyl)-1,1’biphenyl, B
4,4’-bis(chloromethyl)-1,1’-biphenyl (13.1 g, 52 mmol, 1 eq) A, was added in small portions to a suspension of NaCN (5.35 g, 0.109 mmol, 2.05 eq) in DMSO (50 mL) while stirring. While adding A the suspension will turn pale yellow. After adding of A the mixture was heated under stirring at 323 K for 8 h and afterwards stirred for 36 h at room temperature. The now orange-brown suspension was poured in iced water (500 mL) and a yellow solid precipitated, which was stirred further for 30 min. After filtration and washing with iced water (500 mL) the filter cake was dried over night at 323 °C in vacuum to afford the desired intermediate B (10.9 g, 90 %) (¹H-NMR (200 MHz, DMSO-D₆): σ 4.08 (s, 2H, -CH₂-), 7.44 & 7.71 (d, 8H, -CH-). EI-MS at 100 °C (M = C₁₆H₁₂N₂ (232.29) m/z (%) 232 (100) [M], 192 (78) [M - CH₂-CN], 152 (19) [M - 2x CH₂-CN].

References:

Makhloufi, Gamall;Francis, Biju;Dechnik, Janina;Strzelczyk, Alexander;Janiak, Christoph [Polyhedron,2017,vol. 127,p. 59 - 67] Location in patent:supporting information

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143-33-9 Synthesis