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词条 Benzenesulfonyl chloride
释义

  1. References

{{Chembox
| ImageFile = Benzene sulfochloride.svg
| ImageSize =
| ImageAlt =
| PIN = Benzenesulfonyl chloride
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 98-09-9
| PubChem = 7369
| ChemSpiderID = 7091
| InChI = 1/C6H5ClO2S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H
| InChIKey = CSKNSYBAZOQPLR-UHFFFAOYAR
| StdInChI = 1S/C6H5ClO2S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H
| StdInChIKey = CSKNSYBAZOQPLR-UHFFFAOYSA-N
| SMILES = C1=CC=C(C=C1)S(=O)(=O)Cl}}
|Section2={{Chembox Properties
| Formula = C6H5ClO2S
| MolarMass = 176.62
| Appearance = colourless viscous liquid
| Density = 1.384 g/mL at 25 °C(lit.)
| MeltingPtC = 13 to 14
| MeltingPt_notes =
| BoilingPt =
| Solubility = reacts}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}

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.

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}}

3 : Reagents for organic chemistry|Sulfonyl halides|Phenyl compounds

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