chloranil

Chloranil, also known as tetrachloro-1,4-benzoquinone or 2,3,5,6-tetrachloro-p-benzoquinone, is an organic compound with the chemical formula C6Cl4O2. It is a yellow crystalline solid. Chloranil is a derivative of para-benzoquinone where all four hydrogen atoms have been replaced by chlorine atoms.

It can be synthesized by the chlorination of hydroquinone or p-benzoquinone. Another common method involves the oxidation of 2,3,5,6-tetrachloroaniline.

Chloranil is known for its use as an oxidizing agent in organic synthesis. It is employed in dehydrogenation reactions, such as the conversion of dihydroaromatic compounds to aromatic compounds, and in the oxidation of phenols. It also finds applications as a charge-transfer complexing agent and has been studied for its semiconductor properties.

Historically, chloranil was used as a fungicide and a seed treatment, although these applications have largely been superseded by more modern compounds due to environmental and health concerns. It can cause skin irritation and is considered an irritant. Proper handling precautions are necessary when working with chloranil.