Diazald
Diazald is used as a relatively safe and easily handled precursor to diazomethane, which is toxic and unstable. Since its introduction in 1954, Diazald has become the favored commercially available precursor for the synthesis of diazomethane, compared to reagents like N-methyl-N-nitrosourea and N-methyl-N
Upon the addition of a base such as sodium hydroxide or potassium hydroxide and mild heating in a mixture of water, diethyl ether, and a high boiling polar cosolvent, the N-nitrososulfonamide undergoes successive elimination reactions to produce diazomethane as well as a p-toluenesulfonate salt as a byproduct, according to the following mechanism:
Like other nitroso compounds, it is thermally sensitive, as a result of its weak N–NO bond whose bond dissociation energy was measured to be 33.4 kcal/mol.