Methanesulfonic anhydride
[CAS# 7143-01-3]

Identification

• Classification: Organic raw materials >> Organic sulfur compound
• Name: Methanesulfonic anhydride
• Synonyms: methylsulfonyl methanesulfonate
• Molecular Formula: C₂H₆O₅S₂
• Molecular Weight: 174.19
• CAS Registry Number: 7143-01-3
• EC Number: 230-442-1
• SMILES: CS(=O)(=O)OS(=O)(=O)C

Properties

• Melting point: 64-67 ºC
• Boiling point: 125 ºC (4 mmHg)

Safety Data

• Hazard Symbols: GHS05 Danger
• Hazard Statements: H314
• Precautionary Statements: P260-P264-P280-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P321-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1A	H314
Skin corrosion	Skin Corr.	1B	H314
Skin corrosion	Skin Corr.	1	H314
Serious eye damage	Eye Dam.	1	H318

• Transport Information: UN 3261

Discovory and Applicatios

Methanesulfonic anhydride, also known as methanesulfonic acid anhydride or mesyl anhydride, is a sulfonic acid derivative characterized by its unique structure, which consists of two methanesulfonic acid molecules linked through an oxygen atom. It is an important reagent in organic synthesis, particularly known for its ability to facilitate various chemical reactions.

The discovery of methanesulfonic anhydride can be traced back to the research conducted on methanesulfonic acid, which was first synthesized in the early 20th century. The conversion of methanesulfonic acid into its anhydride form was achieved through the removal of water, resulting in a more reactive compound. This transformation opened up new avenues for its application in organic chemistry, allowing chemists to explore its utility as a versatile electrophilic reagent.

Methanesulfonic anhydride has found significant applications in the field of organic synthesis, particularly in the formation of sulfonamide derivatives. It acts as an efficient acylating agent, capable of introducing the methanesulfonyl group into various substrates. This reaction is particularly valuable in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals, where the introduction of sulfonyl groups can enhance biological activity or modify the properties of the resulting compounds.

Additionally, methanesulfonic anhydride is utilized in the preparation of sulfonic esters and sulfonyl chlorides. These derivatives are important intermediates in the synthesis of various organic compounds, contributing to the development of diverse chemical entities. The ability to generate sulfonyl groups selectively makes this reagent a crucial component in many synthetic pathways.

The stability and compatibility of methanesulfonic anhydride with various functional groups also contribute to its widespread use in laboratory settings. Its mild reactivity allows for the functionalization of sensitive substrates without the risk of undesirable side reactions, making it an attractive option for chemists seeking to optimize reaction conditions.

Moreover, methanesulfonic anhydride has been explored in the context of polymer chemistry, where it serves as a reagent for the functionalization of polymers and the modification of polymer surfaces. This application is particularly relevant in the development of advanced materials with tailored properties for specific uses.

In summary, the discovery of methanesulfonic anhydride and its subsequent applications in organic synthesis and materials science underscore its importance as a versatile reagent. Its ability to facilitate the introduction of sulfonyl groups into various substrates has established it as a valuable tool for chemists working in diverse fields.

References

2023. Carbocation Catalysis in the Synthesis of Heterocyclic Compounds. Chemistry of Heterocyclic Compounds, 59(2).
DOI: 10.1007/s10593-023-03157-3

2021. Methanesulfonic anhydride-promoted sustainable synthesis of thioesters from feedstock acids and thiols. Journal of Chemical Sciences, 133(2).
DOI: 10.1007/s12039-020-01871-5

2012. A novel method for the one-pot conversion of carboxylic acids to N,N-dimethylamides. Journal of the Iranian Chemical Society, 9(3).
DOI: 10.1007/s13738-012-0112-5