Dinitro-ortho-cresol

Dinitro-ortho-cresol (DNOC) is an organic compound with the structural formula CH3C6H2(NO2)2OH. It is a yellow solid that is only slightly soluble in water. It is extremely toxic to humans and was previously used as a herbicide and insecticide.

Preparation
This compound is prepared by disulfonation of o-cresol. The resulting disulfonate is then treated with nitric acid to give DNOC. A variety of related derivatives are known including those where the methyl group is replaced by sec-butyl (dinoseb), tert-butyl (dinoterb), and 1-methylheptyl (dinocap). These are prepared by the direct nitration of the alkyphenols.

Applications and safety
DNOC is an uncoupler, which means that it interferes with adenosine triphosphate (ATP) production, making it extremely toxic to humans.

DNOC was one of the earliest pesticides developed, being used as an insecticide since the 1890s and a herbicide since the 1930s. It was banned for use as a pesticide in the United States in 1991.

Symptoms of dinitro-ortho-cresol poisoning, due to ingestion or other forms of exposure, include confusion, fever, headache, shortness of breath, and sweating.