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The compound is prepared by the chlorsulfonation of benzene: C 6 H 6 + 2SHO 3 SCl → C 6 H 5 SO 2 Cl + HCl + SO 3. 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]
Benzenesulfonic acid (conjugate base benzenesulfonate) is an organosulfur compound with the formula C 6 H 6 O 3 S.It is the simplest aromatic sulfonic acid.It forms white deliquescent sheet crystals or a white waxy solid that is soluble in water and ethanol, slightly soluble in benzene and insoluble in nonpolar solvents like diethyl ether.
C 6 H 5 SO 2 Cl + Na 2 SO 3 + H 2 O → C 6 H 5 SO 2 H + NaCl + NaHSO 4. Many other methods have been reported for production of sulfinic acids such as the use tin(II) chloride, or the Grignard reagent with sulfur dioxide. [4] The preparation of sulfinic acids by the oxidation of thiols is difficult due to overoxidation.
General structure of a sulfonic acid with the functional group indicated in blue. In organic chemistry, sulfonic acid (or sulphonic acid) refers to a member of the class of organosulfur compounds with the general formula R−S(=O) 2 −OH, where R is an organic alkyl or aryl group and the S(=O) 2 (OH) group a sulfonyl hydroxide. [1]
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).
The original synthesis of PAES involved electrophilic aromatic substitution of an diaryl ether with the bis (sulfonyl chloride) of benzene. Reactions typically use a Friedel-Crafts catalyst, such as ferric chloride or antimony pentachloride: n O(C 6 H 5) 2 + n SO2Cl2 → {[O(C 6 H 4) 2]SO 2} n + 2n HCl
N-tert-Butylbenzenesulfinimidoyl chloride reacts with enolates, amides, and primary alkoxides by the same general mechanism. The Swern oxidation , which converts primary and secondary alcohols to aldehydes and ketones, respectively, also uses a sulfur-containing compound ( DMSO ) as the oxidant and proceeds by a similar mechanism.
Trifluoromethanesulfonyl chloride (or triflyl chloride, CF3SO2Cl) can be used in a highly efficient method to introduce a trifluoromethyl group to aromatic and heteroaromatic systems, including known pharmaceuticals such as Lipitor. The chemistry is general and mild, and uses a photoredox catalyst and a light source at room temperature. [27]