isonicotinonitrile

Isonicotinonitrile, also known as 4-cyanopyridine, is an organic compound with the chemical formula C6H4N2. It is a derivative of pyridine, where a cyano group (-CN) is attached to the carbon atom at the 4-position of the pyridine ring. This compound is a colorless to pale yellow crystalline solid at room temperature.

Isonicotinonitrile is an important intermediate in the synthesis of various organic compounds, particularly pharmaceuticals and agrochemicals. Its reactivity stems from the presence of both the pyridine ring and the cyano group, allowing for a range of chemical transformations. The nitrogen atom in the pyridine ring can participate in coordination chemistry, while the cyano group can undergo hydrolysis, reduction, or addition reactions.

One of the primary uses of isonicotinonitrile is in the production of isonicotinic acid and its derivatives, which are precursors to drugs like isoniazid, a key medication for treating tuberculosis. It is also employed in the synthesis of other biologically active molecules and specialty chemicals.

The synthesis of isonicotinonitrile typically involves the ammoxidation of 4-methylpyridine (gamma-picoline). This process uses ammonia and oxygen in the presence of a catalyst at elevated temperatures to convert the methyl group into a cyano group. Isonicotinonitrile is soluble in many organic solvents and has a relatively high melting point. Its handling and storage require standard laboratory precautions for organic chemicals.