Benzenesulfonyl chloride

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.

Benzenesulfonyl chloride

Names
Preferred IUPAC name Benzenesulfonyl chloride
Identifiers
CAS Number	98-09-9 Y
3D model (JSmol)	Interactive image
ChemSpider	7091
ECHA InfoCard	100.002.397
PubChem CID	7369
UNII	OI9V0QJV9N Y
CompTox Dashboard (EPA)	DTXSID1026619
InChI 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
SMILES C1=CC=C(C=C1)S(=O)(=O)Cl
Properties
Chemical formula	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)
Solubility in water	reacts
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Production

The compound is prepared by the chlorsulfonation 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. 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