Diazodiphenylmethane

Diazodiphenylmethane is an organic reagent with the chemical formula C₁₃H₁₀N₂. It exists as red-black crystals that melt just above room temperature.

Preparation

Diazodiphenylmethane can be synthesized via the oxidation of benzophenone hydrazone with mercury(II) oxide in diethyl ether and the presence of a basic catalyst. An improved procedure involves dehydrogenation with oxalyl chloride.

Uses

It can be used to synthesize methyl esters and ethers with carboxylic acids and alcohols respectively.
It can also generate methyl carbene and nitrogen gas upon illumination by ultraviolet light or by heating. It can also be electrolyzed form a Ph₂CN anion, which can decompose to form a Ph₂C⁻ anion radical. If carried out in dimethylformamide and tetrabutylammonium perchlorate, these can react to form benzophenone azine, which has the formula Ph₂C=N-N=CPh₂.