Methyl azide

Methyl azide can be prepared by the methylation of sodium azide, for instance with dimethyl sulfate in alkaline solution, followed by passing through a tube of anhydrous calcium chloride or sodium hydroxide to remove contaminating hydrazoic acid.[1] The first synthesis was reported in 1905.[2]

It decomposes in a first-order reaction:[3]

CH₃N₃ → CH₃N + N₂

Methyl azide might be a potential precursor in the synthesis of prebiotic molecules via nonequilibrium reactions on interstellar ices initiated by energetic galactic cosmic rays (GCR) and photons.[4]

Methyl azide is stable at ambient temperature but may explode when heated. Presence of mercury increases the sensitivity to shock and spark. It is incompatible with methanol and dimethyl malonate.[5] When heated to decomposition, it emits toxic fumes of NO_x. It can be stored indefinitely in the dark at −80 °C.[1]

• Graner, G.; Hirota, E.; Iijima, T.; Kuchitsu, K.; Ramsay, D. A.; Vogt, J.; Vogt, N. (1999). "CH₃N₃ Methyl azide". In Kuchitsu, K. (ed.). Group II Molecules and Radicals: Numerical Data and Functional Relationships in Science and Technology. Landolt-Börnstein - Group II Molecules and Radicals. 25 B. p. 1. doi:10.1007/10653318_320. ISBN 3-540-63645-5.
• "Methyl azide". NIST Webbook. National Institute for Standards and Technology.