Methanesulfonamide is a chemical compound and the simplest representative of the substance group of sulfonic acid amides.
Methanesulfonamide is prepared by reacting methanesulfonyl chloride with ammonia. Alternatively, the compound can be obtained by reacting the magnesium salt of methanesulfonic acid with hydroxylamine-O-sulfonic acid or by reduction (here: the Staudinger reaction) of methanesulfonyl azide with triphenylphosphine in methanol.
From a solution of methanesulfonamide in heptane, single crystals of the compound are obtained as semi-transparent, white tablets. X-ray structure analysis yields an OâÂÂSâÂÂO valence angle of 119ð, which deviates significantly from the tetrahedral angle of 109.47ð. At 161 picometers, the sulfurâÂÂnitrogen bond length is significantly shorter than that of a typical single bond (173 picometers) and corresponds to the shortened bond length observed in other sulfonamides. This is presumably caused by a coordinative bond between the lone pair of the amino group and the atomic orbital of the sulfur atom.
Various reagents for chemical syntheses can be produced from methanesulfonamide. For example, methanesulfonamide 1, p-toluenesulfonic acid 2 and 1,1-dimethoxy-2-(methylthio)ethane 3 yield N-(2-methylthio-1-p-toluenesufonylethyl)methanesulfonamide 4, a key compound in the synthesis of symmetrically substituted porphyrins.
In Sharpless dihydroxylation, the oxidation of olefins with potassium hexacyanidoferrate(III) and osmium(VIII) oxide to cis-vicinal-diols, methanesulfonamide acts as a catalyst in the final hydrolysis step during protonation of the osmium intermediate.