Synthesis of benzene sulfonyl chloride

Preparation of benzene sulfonyl chloride (phenylsulfonyl chloride; benzene sulfochloride; benzenesulfonic chloride; benzenosulfochloride)

Preparation of benzene sulfonyl chloride by chlorination with phosphorus pentachloride

Preparation of benzene sulfonyl chloride by chlorination with phosphorus pentachloride

Preparation of benzene sulfonyl chloride by chlorination with phosphorus pentachloride

In a 1-liter flask are mixed 250 g (2.5 moles) of phosphorus pentachloride with 450 g (5 moles) of dry sodium benzene sulfonate (theory calls for 1 mole of pentachloride to 3 moles of sodium benzene sulfonate) and the mixture heated on an oil bath for 5-7 hours at a temperature of 150-170° C. To the flask is attached a reflux condenser so that no volatile matter will be lost. At the end of this time, the mixture is cooled and a liter of water added. A layer of benzene sulfonyl chloride which sinks to the bottom is separated, washed once with water and vacuum distilled in order to purify. The solid impurities are left in the distilling flask, meanwhile, 330 g (70%) of pure benzene sulfonyl chloride which boils between 145-150/45 mm are obtained.

Preparation of benzene sulfonyl chloride by chlorination with phosphorus oxychloride

Preparation of benzene sulfonyl chloride by chlorination with phosphorus oxychloride

Preparation of benzene sulfonyl chloride by chlorination with phosphorus oxychloride

The directions as described under benzene sulfonyl chloride are followed exactly except that the following materials are mixed, 270 g (3 moles) of sodium benzene sulfonate, 230 g (2.75 moles) of phosphorus oxychloride (theory calls for 2 moles of sodium benzene sulfonate to 1 mole of phosphorus oxychloride). The yield of vacuum distilled material boiling between 145-150/45 amounts to 195 g (75% theory).

Organic Chemical Reagents, by A. Roger, 67-71, 1919

IUPAC Name

benzenesulfonyl chloride

InChI

InChI=1S/C6H5ClO2S/c7-10(8,9)6-4-2-1-3-5-6/h1-5H

InChI Key

CSKNSYBAZOQPLR-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)S(=O)(=O)Cl

MeSH Synonyms

benzenesulfonyl chloride

Depositor-Supplied Synonyms

BENZENESULFONYL CHLORIDE, 98-09-9, Phenylsulfonyl chloride, Benzene sulfochloride, Benzenesulfonic chloride, Benzenosulfochloride, Benzene sulfonechloride, Benzenosulfochlorek, Benzenesulphonyl chloride, Benzolsulfochloride, Benzenesulfochloride, Benzenesulfonic acid chloride, Benzenesulfonic(acid)chloride, BSC-refine D, Benezenesulfochloride, Benzenosulphochloride, phenylsulfonylchloride, Benzenesulfon chloride, phenyl sulfonyl chloride, NSC 2864, Benzene sulphonyl chloride, UNII-OI9V0QJV9N, RCRA waste no. U020, RCRA waste number U020, benzene-1-sulfonyl chloride, Benzenosulfochlorek [Polish], Benzenesulfonic (acid) chloride, BENZENE SULFONYL CHLORIDE, HSDB 6004, chlorophenylsulfone, CSKNSYBAZOQPLR-UHFFFAOYSA-N, EINECS 202-636-6, SBB040880, UN2225, BRN 0606926, AI3-18043, 114415-79-1, benzolsulfonylchlorid, Benzenesulfonylchloride, benzensulfonyl chloride, benzenesulphonylchloride, benzene sulfonylchloride, benzenesulfonyl-chloride, phenylsulphonyl chloride, benzenesuIfonyl chloride, PubChem10441, phenyl-sulfonyl chloride, benzene sulphonylchloride, benzenesulfonoyl chloride, benzene-sulfonyl chloride, WLN: WSGR, AC1L1OLS, AC1Q3VLY, 4-benzenesulfonyl chloride, DSSTox_CID_6619, OI9V0QJV9N, 4-benzene sulfonyl chloride, AC1Q6V2L, DSSTox_RID_78165, DSSTox_GSID_26619, SCHEMBL17223, Sulfonyl chloride polymer-bound, 108111_ALDRICH, 108138_ALDRICH, CHEMBL1479161, NSC2864, MolPort-000-872-042, BENZENESULFONYL CHLORIDE KIT, NSC-2864, Tox21_200143, ANW-13664, AR-1H8866, AR3950, STL283941, Benzenesulfonyl chloride polymer-bound, AKOS000118823, EBD2202248, MCULE-6288986714, RP23822, RTR-017685, TRA0097403, CAS-98-09-9, NCGC00090988-01, NCGC00090988-02, NCGC00090988-03, NCGC00090988-04, NCGC00257697-01, AN-24476, BC204660, KB-47565, LS-32134, B0036, B1211, FT-0622639, ST50214477, 9585-EP2308872A1, 9585-EP2316829A1, 22543-EP2275407A1, 22543-EP2275412A1, 22543-EP2277880A1, 22543-EP2280000A1, 22543-EP2284157A1, 22543-EP2292593A2, 22543-EP2292610A1, 22543-EP2295406A1, 22543-EP2295414A1, 22543-EP2295416A2, 22543-EP2295433A2, 22543-EP2298738A1, 22543-EP2298748A2, 22543-EP2298779A1, 22543-EP2301918A1, 22543-EP2305646A1, 22543-EP2311842A2, 22543-EP2314581A1, 22543-EP2314593A1, 38267-EP2270006A1, 38267-EP2311802A1, 60463-EP2298734A2, 60463-EP2308873A1, Benzene sulfonyl chloride [UN2225] [Corrosive], 112943-EP2295437A1, 112943-EP2298775A1, A845807, Benzene sulfonyl chloride [UN2225] [Corrosive], 3B4-3192, Amberlite® XE-305 sulfonic acid chloride form, I01-1994, I14-111457, InChI=1/C6H5ClO2S/c7-10(8,9)6-4-2-1-3-5-6/h1-5

Removed Synonyms

CID7369, 4-11-00-00049 (Beilstein Handbook Reference), 2040-07-5

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