Applications of Methanesulfonyl chloride

Methanesulfonyl chloride is a compound containing a sulfonyl chloride used to make methanesulfonates and to generate sulfene.
Methanesulfonyl chloride is awful toxic, damp sensitive, corrosive, and a lachrymator. It should be stored in a dry location, finer in a desiccator. It is bogus either via absolute admixture from methane and sulfuryl chloride in a abolitionist reaction.
other adjustment of accomplish starts with methanesulfonic acid, which is attainable out of methane and sulfur trioxide or by active blaze of methanethiol
The methanesulfonic acerbic able is reacted with thionyl chloride or phosgene to anatomy mesyl chloride
Applications
Methanesulfonates
The capital use of Methanesulfonyl chloride is the accumulation of methanesulfonates from alcohols in the attendance of a non-nucleophilic base. Methanesulfonates are acclimated as intermediates in barter reactions, abolishment reactions, reductions, and barter reactions. When advised with a Lewis acid, oxime methanesulfonates will abide a accomplished Beckmann rearrangement.
Methanesulfonates accept been occasionally acclimated as a attention accumulation for alcohols. It is abiding to acerb altitude and is broken aback to the booze application sodium amalgam.
Methanesulfonamides
Methanesulfonyl chloride will acknowledge with amines to anatomy a methanesulfonamide. Unlike a methanesulfonate, a methanesulfonamide is a actual abiding anatomic accumulation beneath both acerb and basal conditions. When acclimated as a attention group, they can be adapted aback to amines application lithium aluminium hydride or a abandoning metal reduction.
Addition to alkynes
In the attendance of copper(II) chloride, methanesulfonyl chloride will add beyond alkynes to anatomy β-chloro sulfones.
Accumulation of heterocycles
Upon analysis with a base, such as triethylamine, methanesulfonyl chloride will abide an abolishment to anatomy sulfene. Sulfene can abide cycloadditions to anatomy assorted heterocycles. α-Hydroxyketones acknowledge with sulfene to anatomy five-membered sultones.
Miscellaneous
Forming acyliminium ions from α-hydroxyamides can be done application methanesulfonyl chloride and a base, about triethylamine.
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