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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.
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.
Hazard Statements: H314
Causes severe skin burns and eye damage.
Precautionary Statements: P260-P264b-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant