Benzenesulfonyl chloride
Names
Preferred IUPAC name
Benzenesulfonyl chloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.397
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).
Infobox references

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.

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.

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

References

  1. ↑ Roger Adams, C. S. Marvel, H. T. Clarke, G. S. Babcock, and T. F. Murray "Benzenesulfonyl chloride" Org. Synth. 1921, vol. 1, p. 21. doi:10.15227/orgsyn.001.0021
  2. ↑ 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. ISBN 978-0-471-21503-5
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