Benzenesulfonyl Chloride
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Benzenesulfonyl Chloride
Benzenesulfonyl chloride
Benzene sulfochloride.svg
Names
Preferred IUPAC name
Benzenesulfonyl chloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.397
Properties
C6H5ClO2S
Molar mass 176.62
Appearance colourless viscous 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.

Chlorsulfonic acid synthesis.svg

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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