General Description
A liquid. Density 1.56 g/cm3. Flash point exceeds 230°F.
Reactivity Profile
2-CHLOROETHANESULFONYL CHLORIDE is incompatible with strong oxidizing agents, alcohols, amines, alkali. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291].
Air & Water Reactions
Reacts with water to produce corrosive and toxic gaseous hydrogen chloride.
Chemical Properties
CLEAR SLIGHTLY YELLOW TO BROWN LIQUID
Uses
2-Chloroethanesulfonyl chloride was used in one-pot sulfonylation/intramolecular thia-Michael protocol for the synthesis of 1,5,2-dithiazepine 1,1-dioxides. It was also used in synthesis of vinyl sulfonamides with a furan, carbocyclic, semi cyclic or acyclic 1,3-diene moiety.
Application
As a precursor of the bis-electrophilic synthon vinylsulfonyl chloride, 2-chloroethanesulfonyl chloride can react with a wide range of bis-nucleophilic synthons, such as substituted 2-amino alcohols, to generate 7-membered sultams. This compound can be used in lieu of vinylsulfonyl chloride via a domino elimination– amidation reaction[1-2].
References
[1] Qin Zang. “Synthesis of a Library of 1,5,2-Dithiazepine 1,1-Dioxides. Part 1: A One-Pot Sulfonylation/Thia-Michael Protocol.” Heterocycles 86 2 (2012).
[2] Victor O Rogachev, Peter Metz. “Thermal and high pressure intramolecular Diels–Alder reaction of vinylsulfonamides.” Nature Protocols 1 6 (2007): 3076–3087.
