Methanesulfonic anhydride is used to prepare methylsulfonyl esters called as mesylates. It finds application in the reaction of aromatic alkylation. It reacts with dimethylsulfoxide to get sulfoxonium complex, which is a useful oxidizing agent.
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Applications
Methanesulfonic anhydride is used to prepare methylsulfonyl esters called as mesylates. It finds application in the reaction of aromatic alkylation. It reacts with dimethylsulfoxide to get sulfoxonium complex, which is a useful oxidizing agent.
Solubility
Soluble in organic solvents.
Notes
Moisture sensitive. Hygroscopic. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents.
RUO – Research Use Only
More powerful sulfonylating reagent than the sulfonyl chloride, also avoiding possible displacement of sulfonate by halide. With a catalytic amount of the acid effects mesylation of deactivated aromatics such as 1,3-dichlorobenzene: Chem. Lett., 395 (1988); mesyl chloride is ineffective.
Primary and secondary alcohols may be oxidized to carbonyl compounds by sulfonic anhydrides in DMSO: J. Org. Chem., 39, 1977 (1974). For related methods, see Dimethyl sulfoxide, A13280.
Liu, W., Tilley, T. D. Sterically Controlled Functionalization of Carbon Surfaces with- C6H4CH2X (X= OSO2Me or N3) Groups for Surface Attachment of Redox-Active Molecules. Langmuir 2015, 31 (3), 1189-1195.
Hu, Y.; Zhang, F.; Zhang, C.; Zhang, M. Anti-inflammatory Properties of an Active Sesquiterpene Lactone and its Structure-Activity Rela-tionship. Med chem 2015, 5, 354-360.