metaphthalonitrile

Metaphthalonitrile, also known as 1,3-dicyanobenzene, is an organic compound with the chemical formula C8H4N2. It is a dinitrile, meaning it contains two nitrile (-CN) functional groups. In metaphthalonitrile, these nitrile groups are attached to a benzene ring in a meta (1,3) position relative to each other.

This colorless solid typically appears as crystalline powder and has a molecular weight of 128.13 g/mol. Its melting point is around 160-163 °C. Metaphthalonitrile is generally insoluble in water but soluble in many organic solvents. It is a derivative of isophthalonitrile, which is its isomer with nitrile groups in the 1,2 (ortho) or 1,4 (para) positions.

Metaphthalonitrile serves as a precursor and intermediate in the synthesis of various organic compounds. Its reactive nitrile groups can undergo a range of chemical transformations, including hydrolysis to form carboxylic acids, reduction to amines, and participation in cycloaddition reactions. These properties make it valuable in the production of polymers, pharmaceuticals, and other fine chemicals. It can be synthesized through methods such as the dehydration of isophthalimide or the ammoxidation of m-xylene.