2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

[5] DDQ decomposes in water, but is stable in aqueous mineral acid.

[7] The substance did not receive interest until its potential as a dehydrogenation agent was discovered.

The stoichiometry of its action is illustrated by the conversion of tetralin to naphthalene: The resulting hydroquinone is poorly soluble in typical reaction solvents (dioxane, benzene, alkanes), which facilitates workup.

Solutions of DDQ in benzene are red, due to the formation of a charge-transfer complex.

[9] DDQ reacts with water to release highly toxic hydrogen cyanide (HCN).

Structural formula of dichlorodicyanobenzoquinone
Space-filling model of the dichlorodicyanobenzoquinone molecule