Benzylsulfonyldiazomethane

[1588-80-3] C8H8N2O2S {MW 196.22) InChI = 1S/C8H8N2O2S/c9-10-7-13(11,12)6-8-4-2-1-3-5-8/h1-5,7H,6H2 InChIKey = FONISQCLDPCMQU-UHFFFAOYSA-N (safe, nonexplosive, shelf-stable substitute for diazomethane;2 performs similar reactions such as ring expansions3 and Arndt–Eistert syntheses;4 enables the preparation of various substituted benzyl sulfones) Alternate Name: BSDM. Physical Data: mp 98–99 °C; bright yellow solid. Solubility: sol halogenated organic solvents. Form Supplied in: not available commercially. Preparative Methods: from the corresponding urethane via nitrosation with nitrosyl chloride followed by rearrangement on neutral alumina,2 or via reaction of ethyl benzylsulfonylacetate with tosyl azide in the presence of triethylamine.5 Handling, Storage, and Precautions: no toxicological data available; nonexplosive; stable for over 4 months at −20 °C. Use in a fume hood.