Some common heterocyclic compound, 935-02-4, name is 3-Phenylpropiolonitrile, molecular formula is C9H5N, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of 3-Phenylpropiolonitrile
4.3.1 (Z)-3-(3-Methyl-2-thioxo-2,3-dihydro-1H-imidazol-1-yl)-3-phenyl-2-propenenitrile (3a) To a mixture of acetylene 2 (127 mg, 1 mmol) and S (32 mg, 1 mmol) was added 1-methylimidazole (1a; 82 mg, 1 mmol). The mixture was stirred at 20-25 C for 24 h. Column chromatography afforded thione 3a (132 mg, 67%), yellow microcrystalline powder, mp 159-161 C (washed with ether). Initial imidazole 1a was recovered (15 mg, conversion was 82%). 1H NMR (400.13 MHz, CDCl3): delta=7.45-7.25 [m, 5H, Ho,m,p from C(6)-Ph], 6.89 (s, 1H, 4-H), 6.80 (s, 1H, 5-H), 6.05 (s, 1H, 7-H), 3.63 (s, 3H from N-CH3) ppm. 13C NMR (100.62 MHz, CDCl3): delta=164.4 (C-2), 154.2 (C-6), 132.5 [Ci from C(6)-Ph], 131.8 [Cp from C(6)-Ph], 129.1 [Cm from C(6)-Ph], 126.8 [Co from C(6)-Ph], 119.8 (C-4), 116.9 (C-5), 114.6 (CN), 97.0 (C-7), 35.3 (N-CH3) ppm. 15N NMR (40.55 MHz, CDCl3): delta=-110.6 (CN), -207.8 (N-3), -217.9 (N-1) ppm. IR (KBr): 2220 (CN), 1621 (C=C), 1383 (C=S) cm-1. Anal. Calcd for C13H11N3S (241.31): C, 64.70; H, 4.59; N, 17.41; S, 13.29. Found: C, 64.44; H, 4.32; N, 17.72; S, 13.34.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 935-02-4, its application will become more common.
Reference:
Article; Belyaeva, Kseniya V.; Andriyankova, Ludmila V.; Nikitina, Lina P.; Mal’Kina, Anastasiya G.; Afonin, Andrei V.; Ushakov, Igor A.; Bagryanskaya, Irina Yu.; Trofimov, Boris A.; Tetrahedron; vol. 70; 5; (2014); p. 1091 – 1098;,
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