2-Mesitylenesulfonyl chloride
[CAS# 773-64-8]

Identification

• Classification: Biochemical >> Nucleoside drugs >> Nucleotides and their analogues
• Name: 2-Mesitylenesulfonyl chloride
• Synonyms: Mesitylenesulfonyl chloride; 2,4,6-Trimethylbenzenesulfonyl chloride
• Molecular Formula: C₉H₁₁ClO₂S
• Molecular Weight: 218.70
• CAS Registry Number: 773-64-8
• EC Number: 212-257-8
• SMILES: CC1=CC(=C(C(=C1)C)S(=O)(=O)Cl)C

Properties

• Solubility: insoluble (water)
• Melting point: 53-57 ºC
• Boiling point: 150 ºC
• Flash point: 113 ºC

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.	1B	H314
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Serious eye damage	Eye Dam.	1	H318
Skin corrosion	Skin Corr.	1	H314

• Transport Information: UN 3261

Discovory and Applicatios

2-Mesitylenesulfonyl chloride, also known as mesitylene sulfonyl chloride, was first synthesized in the early 20th century as part of research into organic sulfonamide compounds. Chemists sought to develop efficient methods for introducing sulfonyl chloride groups into aromatic molecules, leading to the discovery of 2-Mesitylenesulfonyl chloride. Its synthesis involved the reaction of mesitylene (1,3,5-trimethylbenzene) with sulfur trioxide followed by chlorination, resulting in the formation of the sulfonyl chloride derivative. This discovery marked a significant advancement in organic synthesis methodology, providing a versatile reagent for the preparation of various sulfonamide derivatives and other organic compounds.

2-Mesitylenesulfonyl chloride is widely used as a reagent in organic synthesis for the preparation of sulfonamide derivatives. By reacting with amines or other nucleophiles, it forms sulfonyl amides, which are valuable intermediates in the synthesis of pharmaceuticals, agrochemicals, and specialty chemicals. 2-Mesitylenesulfonyl chloride participates in sulfonylation reactions, where the sulfonyl chloride group is transferred to nucleophilic substrates such as alcohols, phenols, and heteroatoms. These reactions enable the introduction of the sulfonyl functional group into organic molecules, allowing for the synthesis of diverse sulfonamide and sulfonyl-containing compounds.

Sulfonamide derivatives prepared using 2-Mesitylenesulfonyl chloride serve as important building blocks in medicinal chemistry for the development of pharmaceutical agents targeting various diseases and disorders. Sulfonyl amides exhibit diverse biological activities, including antimicrobial, anticancer, and anti-inflammatory properties, making them attractive candidates for drug discovery programs.

2-Mesitylenesulfonyl chloride is employed in polymer chemistry for the synthesis of functionalized polymers with sulfonamide pendant groups. These polymers exhibit unique properties such as ion-exchange capability, proton conductivity, and water solubility, making them useful in applications such as membrane materials for fuel cells, separation technologies, and drug delivery systems.

2-Mesitylenesulfonyl chloride serves as a coupling partner in cross-coupling reactions with various organometallic reagents, such as Grignard reagents or organolithium compounds. These reactions enable the synthesis of biaryl sulfonamide compounds, which are valuable motifs in medicinal chemistry and materials science.

Research into the reactivity and synthetic applications of 2-Mesitylenesulfonyl chloride continues to expand its utility in organic synthesis and chemical research. Efforts focus on developing new methodologies and reaction protocols that utilize this versatile reagent for the synthesis of complex organic molecules and functional materials.