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4,4'-biphenyldiacetonitrile synthesis
- Product Name:4,4'-biphenyldiacetonitrile
- CAS Number:7255-83-6
- Molecular formula:C16H12N2
- Molecular Weight:232.28
![4,4'-Bis(chloromethyl)-1,1'-biphenyl](/CAS/GIF/1667-10-3.gif)
1667-10-3
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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
![Biphenyl](/CAS/GIF/92-52-4.gif)
92-52-4
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![4,4'-biphenyldiacetonitrile](/CAS/20200401/GIF/7255-83-6.gif)
7255-83-6
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