N-methyl-N-nitrosoacetamide

Uses

N-methyl-N-nitrosoacetamide is an alkylating agent; a source of diazomethane; can be used as an activated acylating agent and as a precursor to esters and olefins.

Preparation

Nitrosation of N-alkyl amides with Sodium Nitrite/acid mixtures, Nitrosyl Chloride, or Nitrogen Dioxide. N-Deprotonation of the amide with n-Butyllithium or Sodium Hydride, followed by treatment with nitrosonium salts or Nitrogen Dioxide, is a second approach that is particularly useful in the preparation of thermally labile nitrosoamides.

Safety Profile

Poison by ingestion. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.