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 analogue because it is a solid at room temperature and easier to handle.

Quick Facts Names, Identifiers ...
Benzenesulfonyl chloride
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Names
Preferred IUPAC name
Benzenesulfonyl chloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.397 Edit this at Wikidata
UNII
  • InChI=1S/C6H5ClO2S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H
    Key: CSKNSYBAZOQPLR-UHFFFAOYSA-N
  • InChI=1/C6H5ClO2S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H
    Key: CSKNSYBAZOQPLR-UHFFFAOYAR
  • C1=CC=C(C=C1)S(=O)(=O)Cl
Properties
C6H5ClO2S
Molar mass 176.62
Appearance colourless liquid
Density 1.384 g/mL at 25 °C(lit.)
Melting point 13 to 14 °C (55 to 57 °F; 286 to 287 K)
reacts
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The compound is prepared by the chlorination of benzenesulfonic acid or its salts with phosphorus oxychloride[1] or, less commonly, by a reaction between benzene and chlorosulfuric acid.

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The Hinsberg test for amines involves their reaction with benzenesulfonyl chloride.[2]

References

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