Synthesis of thiophenol

Preparation of thiophenol (benzenethiol; mercaptobenzene; phenyl mercaptan)

Preparation of thiophenol (benzenethiol; mercaptobenzene; phenyl mercaptan)

Preparation of thiophenol (benzenethiol; mercaptobenzene; phenyl mercaptan)

In a 12 liter flask are placed 7200 g of cracked ice and 2400 g of concentrated sulfuric acid (d=1.84). The mixture becomes very cold and is kept at -5 to 0° C by means of an ice-salt bath. Mechanical stirring is started and 600 g of benzene sulfonyl chloride are gradually introduced during 30 minutes period. Then 1200 g of zinc dust are added slowly in portions during the course of about 30 minutes, carefully keeping the temperature low at all times. The contents of the flask are now stirred for 1 to 1,5 hours still keeping the temperature at 0° C or below. A stopper with an efficient reflux condenser (jacket 100 cm long, inner tube 2 cm in diam.) and mechanical stirrer is inserted. The ice bath is then removed and the reaction mixture allowed to warm up, the stirring being continued. Within a very few minutes, a vigorous reaction with the evolution of much hydrogen takes place and it is advisable to cool the flask momentarily by a stream of water. After the first ebullition has subsided, no further attention is required and the mixture is heated to boiling over a ring burner till the solution becomes clear. The stirring should be continued during the refluxing and the stirrer should be so arranged as to suck the liquid downward from the surface. This helps distribute the zinc which floats on top of the liquid. About 7 hours are required for the heating. The thiophenol is then distilled out with steam. The product is separated from the water, dried with calcium chloride for 5 minutes and distilled (boiling 166-169° C). The crude material weighs 359 g (91% theory).

Organic Chemical Reagents, by A. Roger, 71-73, 1919

IUPAC Name

benzenethiol

InChI

InChI=1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H

InChI Key

RMVRSNDYEFQCLF-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)S

MeSH Synonyms

benzenethiol, thiophenate, thiophenol, thiophenol, copper (+1) salt, thiophenol, potassium salt, thiophenol, sodium salt

Depositor-Supplied Synonyms

Benzenethiol, THIOPHENOL, Mercaptobenzene, Phenyl mercaptan, Phenylmercaptan, Phenylthiol, 108-98-5, Phenol, thio-, Thiofenol, RCRA waste number P014, USAF XR-19, Thiofenol [Czech], Benzene, mercapto-, NSC 6953, RCRA waste no. P014, UNII-7K011JR4T0, FEMA No. 3616, CCRIS 8922, CHEBI:48498, HSDB 5387, RMVRSNDYEFQCLF-UHFFFAOYSA-N, EINECS 203-635-3, UN2337, BRN 0506523, AI3-15418, DSSTox_CID_6811, DSSTox_RID_78220, DSSTox_GSID_26811, thiophenate, CAS-108-98-5, benzenthiol, benzene thiol, (phenyl)sulfane, Thio phenol, phenyl hydrosulfide, PubChem5421, SCHEMBL67, AC1L1PYX, WLN: SHR, AC1Q7G9N, C6H6S, T32808_ALDRICH, W361607_ALDRICH, 240249_ALDRICH, CHEMBL119405, 09286_FLUKA, FEMA 3616, TIMTEC-BB SBB040929, NSC6953, MolPort-000-872-091, 7K011JR4T0, LABOTEST-BB LTBB001444, LTBB001444, 930-69-8 (hydrochloride salt), NSC-6953, STR00162, AKOS BBS-00004420, Tox21_201577, Tox21_303257, LS-477, NSC229566, STL263870, AKOS000118794, AN-6506, AS04135, MCULE-4163310418, NSC-229566, Phenyl mercaptan [UN2337] [Poison], RP18988, UN 2337, NCGC00249074-01, NCGC00257036-01, NCGC00259126-01, Phenyl mercaptan [UN2337] [Poison], BP-21352, KB-61709, B0041, V2324, 8387-EP2269993A1, 8387-EP2270009A1, 8387-EP2270114A1, 8387-EP2272817A1, 8387-EP2272839A1, 8387-EP2272840A1, 8387-EP2274983A1, 8387-EP2277862A2, 8387-EP2277881A1, 8387-EP2284165A1, 8387-EP2289509A2, 8387-EP2292596A2, 8387-EP2292597A1, 8387-EP2295437A1, 8387-EP2298775A1, 8387-EP2298776A1, 8387-EP2305808A1, 8387-EP2308812A2, 8387-EP2308840A1, 8387-EP2314576A1, 8387-EP2316824A1, 30241-EP2272839A1, 30241-EP2272840A1, 30241-EP2272972A1, 30241-EP2272973A1, 30241-EP2275404A1, 30241-EP2277872A1, 30241-EP2280001A1, 30241-EP2292601A1, 30241-EP2298739A1, 30241-EP2301911A1, 30241-EP2305695A2, 30241-EP2305696A2, 30241-EP2305697A2, 30241-EP2305698A2, 30241-EP2308812A2, 30241-EP2311464A1, 4-06-00-01463 (Beilstein Handbook Reference), I14-1169, 3B3-033377, InChI=1/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7, 16528-57-7, BT6

Removed Synonyms

thiophenol, sodium salt, thiophenol, potassium salt, SODIUM BENZENETHIOLATE, thiophenol, copper (+1) salt, CID7969, C042983

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