Mesylate

As a mesyl group of covalently bonded rest of methanesulfonic acid ( CH3SO3 ) is called organic compounds. Thus it is the ester of methanesulfonic acid. Your name is derived from its systematic name methanesulfonyl. The compounds are commonly referred to as mesylates and should not be confused with the same salts of methanesulfonic acid ( mesylate ). In structural formulas, the mesyl group is sometimes abbreviated as MS or Mes. The international non-proprietary name of the mesylates is Mesilate. It is structurally related to the triflyl.

Production

Mesylate can be prepared by the reaction of methanesulfonyl chloride with alcohols in the presence of bases:

Properties

The methanesulfonic acid is one of the strong acids. The Mesylation is therefore a weak base, which is good resonance-stabilized:

For this reason, the mesyl group is a good leaving group that can be readily removed by suitable nucleophiles under substitution. Alkyl mesylates are good alkylating agents. Due to their ability to alkylate DNA, the Mesylverbindungen Methansulfonsäureallylester, ethyl methanesulfonate and methyl methanesulfonate are considered possible carcinogens.

Use

In its capacity as a leaving group, the mesyl group applies in preparative organic chemistry. The conversion of alcohols into mesylates the poor leaving group OH in converting a good leaving group, thereby nucleophilic substitution reactions are made possible at this position:

This application is not very atom economical, as always, stoichiometric quantities of waste materials are formed with relatively high molecular mass. Therefore, the synthesis method is mainly used in laboratory scale and scarcely in industrial processes.