Hydrazone

Structure of the hydrazone functional group

Benzophenone hydrazone, an illustrative hydrazone

Carbonyl cyanide m-chlorophenyl hydrazone

A hydrazone is a class of organic compounds with the structure R₁R₂C=NNH₂. They are related to ketones and aldehydes by the replacement of the oxygen with the NNH₂ functional group. They are formed usually by the action of hydrazine on ketones or aldehydes.

Uses

The formation of aromatic hydrazone derivatives is used to measure the concentration of low molecular weight aldehydes and ketones, e.g. in gas streams. For example, dinitrophenylhydrazine coated onto a silica sorbent is the basis of an adsorption cartridge. The hydrazones are then eluted and analyzed by HPLC using a UV detector.

The compound carbonyl cyanide-p-trifluoromethoxyphenylhydrazone (abbreviated as FCCP) is used to "uncouple" ATP synthesis and reduction of oxygen in oxidative phosphorylation in molecular biology.

Hydrazones are reactants in hydrazone iodination, the Shapiro reaction and the Bamford-Stevens reaction to vinyl compounds.