Benzenesulfonyl chloride
Chemical compound
From Wikipedia, the free encyclopedia
Benzenesulfonyl chloride is an organosulfur compound with the formula C6H5SO2Cl. It is a colourless solid 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 for laboratory use because it is a solid at room temperature and easier to handle.
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| Names | |
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| Preferred IUPAC name
Benzenesulfonyl chloride | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.002.397 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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).
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Production
The compound is prepared by the chlorosulfonation of benzene:
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
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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]