isocyanobenzene

Isocyanobenzene, also known as phenyl isocyanide or phenyline, is an organic compound with the chemical formula C6H5NC. It is a colorless liquid with a pungent odor. The molecule consists of a phenyl group (C6H5) attached to an isocyano group (-NC). This arrangement, with the carbon atom directly bonded to the phenyl ring and the nitrogen atom, distinguishes it from its isomer, benzonitrile (C6H5CN), where the phenyl group is bonded to the carbon of the nitrile group.

Isocyanobenzene is a reactive compound and a valuable building block in organic synthesis. It participates in various reactions, including cycloadditions, insertions, and nucleophilic additions. Its reactivity stems from the electrophilic nature of the carbon atom in the isocyano group and the presence of a lone pair on the nitrogen atom.

This compound can be synthesized through several methods, commonly involving the dehydration of N-phenylformamide or the reaction of aniline with chloroform in the presence of a strong base. Due to its toxicity and unpleasant odor, isocyanobenzene is typically handled with caution in well-ventilated areas. Its applications are primarily in research laboratories for the synthesis of heterocyclic compounds, coordination complexes, and other complex organic molecules.