Benzenesulfonyl chloride

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Benzenesulfonyl chloride
Benzene sulfochloride.svg
Names
Preferred IUPAC name
Benzenesulfonyl chloride
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.397 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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
Appearancecolourless 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).

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. [1] The closely related compound toluenesulfonyl chloride is often preferred analogue because it is a solid at room temperature and easier to handle.

Contents

Production

The compound is prepared by the chlorosulfonation of benzene:

C6H6 + 2SHO3SCl → C6H5SO2Cl + HCl + SO3

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. [2]

Reactions

Benzenesulfonyl chloride is an electrophilic reagent. It hydrolyzes with heat but is stable toward cold water. [2] Amines react to give sulfonamides. This reaction is the basis of the Hinsberg test for amines. [3]

References

  1. ↑ Lindner, Otto; Rodefeld, Lars (2000). "Benzenesulfonic Acids and Their Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a03_507. ISBN   978-3-527-30385-4.
  2. 1 2 Roger Adams, C. S. Marvel, H. T. Clarke, G. S. Babcock, and T. F. Murray (1921). "Benzenesulfonyl Chloride". Organic Syntheses. 1: 21. doi:10.15227/orgsyn.001.0021.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ↑ 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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