Benzenesulfonyl chloride is an organosulfur compound with the formula C6H5SO2Cl. It is a colourless viscous oil that dissolves in organic solvents, but reacts with compounds containing reactive N-H and O-H bonds. It is mainly used to prepare sulfonamides and sulfonate esters by reactions with amines and alcohols, respectively. The closely related compound toluenesulfonyl chloride is often preferred for laboratory use because it is a solid at room temperature and easier to handle.
Production The compound is prepared by the chlorosulfonation of benzene:
Benzenesulfonic acid is an intermediate in this conversion. Diphenylsulfone is a side product.
Benzenesulfonyl chloride can also be prepared by treating benzenesulfonate salts with phosphorus oxychloride.
Reactions
Benzenesulfonyl chloride is an electrophilic reagent. It hydrolyzes with heat but is stable toward cold water. Amines react to give sulfonamides. This reaction is the basis of the Hinsberg test for amines.Ralph L. Shriner, Christine K. F. Hermann, Terence C. Morrill, David Y. Curtin, Reynold C. Fuson "The Systematic Identification of Organic Compounds", 8th Edition, 2003, Wiley.
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