Benzenesulfonyl chloride is an
organosulfur compound
Organosulfur chemistry is the study of the properties and synthesis of organosulfur compounds, which are organic compounds that contain sulfur. They are often associated with foul odors, but many of the sweetest compounds known are organosulfur der ...
with the formula C
6H
5SO
2Cl. 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
sulfonamide
In organic chemistry, the sulfonamide functional group (also spelled sulphonamide) is an organosulfur group with the Chemical structure, structure . It consists of a sulfonyl group () connected to an amine group (). Relatively speaking this gro ...
s and
sulfonate esters by reactions with
amine
In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...
s and
alcohol
Alcohol may refer to:
Common uses
* Alcohol (chemistry), a class of compounds
* Ethanol, one of several alcohols, commonly known as alcohol in everyday life
** Alcohol (drug), intoxicant found in alcoholic beverages
** Alcoholic beverage, an alco ...
s, respectively.
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 chlorsulfonation of
benzene
Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...
:
:
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.
Reactions
Benzenesulfonyl chloride is an electrophilic reagent. It hydrolyzes with heat but is stable toward cold water.
[ Amines react to give sulfonamides. This reaction is the basis of the Hinsberg test for ]amine
In chemistry, amines (, ) are organic compounds that contain carbon-nitrogen bonds. Amines are formed when one or more hydrogen atoms in ammonia are replaced by alkyl or aryl groups. The nitrogen atom in an amine possesses a lone pair of elec ...
s.[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]
References
Reagents for organic chemistry
Sulfonyl halides
Phenyl compounds