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Benzenesulfonyl chloride is an organosulfur compound with the formula C 6 H 5 SO 2 Cl. 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 intermediate benzenesulfonic acid can be chlorinated with thionyl chloride as well. Benzenesulfonyl chloride, the most important sulfonyl halide, can also be produced by treating sodium benzenesulfonate with phosphorus pentachlorides. [5] Benzenediazonium chloride reacts with sulfur dioxide and copper(I) chloride to give the sulfonyl chloride:
The Hinsberg reaction is a chemical test for the detection of primary, secondary and tertiary amines.The reaction was first described by Oscar Hinsberg in 1890. [1] [2] In this test, the amine is shaken well with the Hinsberg reagent (benzenesulfonyl chloride) in the presence of aqueous alkali (either KOH or NaOH).
Conversion to the corresponding benzenesulfonyl chloride (C 6 H 5 SO 2 Cl) is effected with phosphorus pentachloride. It is a strong acid, being almost fully dissociated in water. Benzenesulfonic acid and related compounds undergo desulfonation when heated in water near 200 °C.
The reaction of primary and secondary amines with benzenesulfonyl chloride is the basis of the Hinsberg reaction, a method for detecting primary and secondary amines. Sulfonamides undergo a variety of acid-base reactions. The N-H bond can be deprotonated. The alkylsulfonamides can be deprotonated at carbon. Arylsulfonamides undergo ortho ...
benzenesulfonyl chloride: 98-09-9 C 6 H 5 ClSe: phenylselenenyl chloride: 5707-04-0 C 6 H 5 Cl 2 OP: phenylphosphoro dichloridite: 3426-89-9 C 6 H 5 Cl 3 Ge: phenyltrichlorogermane: 1074-29-9 C 6 H 5 Cl 3 Si: phenyl trichlorosilane: 98-13-5 C 6 H 5 Cl 3 Sn: phenyltrichlorostannane: 1124-19-2 C 6 H 5 FO 2 S: benzenesulfonyl fluoride: 368-43-4 C ...
An added drop of ferric chloride will turn the solution an intense red when aldehyde is present. The sulfonamide can be prepared by reaction of hydroxylamine and benzenesulfonyl chloride in ethanol with potassium metal. [3] chelation with iron
This method of synthesizing a sulfonamide is often used for the synthesis of glybuzole. Glybuzole can be synthesized using benzenesulfonyl chloride, 2-amino-5-tert-butyl-1,3,4-thiadiazole and pyridine. [11] The reaction that will proceed is a bimolecular nucleophilic substitution reaction (SN2) (Figure 2).