Diazald

Diazald ("N"-methyl-"N"-nitroso-"p"-toluenesulfonamide) is used as a relatively safe and easily handled precursor to diazomethane, which is toxic and unstable. 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"'-nitro-"N-"nitrosoguanidine, which are less thermally stable and more toxic and mutagenic, respectively.
Upon the addition of a base such as sodium hydroxide or potassium hydroxide and mild heating (65–70 °C) in a mixture of water, diethyl ether, and a high boiling polar cosolvent (e.g., diethylene glycol monomethyl ether), the "N-"nitrososulfonamide undergoes successive elimination reactions to produce diazomethane (which is codistilled as an ethereal solution) 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.