1885-29-6 Usage
Chemical Properties
Yellow Solid
Uses
2-Aminobenzonitrile is used for induction of nitrilase activity in Arthrobacter and for radioprotective agent.
Preparation
2-Aminobenzamide was dehydrated to 2-aminobenzonitrile without protection of the amino group in the presence of phenylphosphonyl dichloride and pyridine. Other structural isomers (3-aminobenzamide and 4-aminobenzamide) did not give corresponding aminobenzonitriles.In this paper, the dehydration reactions of 2-aminobenzamide (1a) to 2-aminobenzonitrile (3a) using phosphoryl chloride (2a), phenyl phosphoryl dichloride (2b), 4-chlorophenyl phosphoryl dichloride (2c) or phenylphosphonic dichloride (2d) in pyridine are reported.The chemical yield and melting point of 2-aminobenzonitrile (3a) obtained by four dehydrating reagents (2a-d) are listed in Table-1. 2-Aminobenzamide was dehydrated by reagents 2a-c to give 2-aminobenzonitrile in the yield lower than 60 %, while the reaction by reagent (2d) gave the highest yield, 96 %. On the other hand, benzamide (1b) without amino groups afforded benzonitrile (3a) in the yield of 43 %.synthesis of aminobenzonitrile by dehydration of aminobenzamide using phenylphosphonic dichloride in pyridine
Synthesis Reference(s)
Journal of the American Chemical Society, 96, p. 5933, 1974 DOI: 10.1021/ja00825a039The Journal of Organic Chemistry, 43, p. 944, 1978 DOI: 10.1021/jo00399a030Tetrahedron Letters, 32, p. 1007, 1991 DOI: 10.1016/S0040-4039(00)74473-X
Safety Profile
Poison by intravenous route. Seealso NITRILES. When heated to decomposition it emitstoxic fumes of NOx and CN- .
InChI:InChI=1/C7H6N2/c8-5-6-3-1-2-4-7(6)9/h1-4H,9H2