Benzenesulfonyl chloride

Benzenesulfonyl chloride
Names
	Preferred IUPAC name Benzenesulfonyl chloride
Identifiers
CAS Number	98-09-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	7091;
ECHA InfoCard	100.002.397
PubChem CID	7369;
UNII	OI9V0QJV9N ;
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

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.

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

^ 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.
^ ^a ^b 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)
^ 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

[Ullmann-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.

[RA-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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