Synthesis of benzyl mercaptan

Preparation of benzyl mercaptan

Preparation of benzyl mercaptan

Preparation of benzyl mercaptan

In a round-bottomed flask, 1 mole of benzyl bromide or benzyl chloride is added to 1.1 mole of thiourea and 50 ml of 95% alcohol, and the mixture is refluxed for 6 hours. On cooling, the benzylthiouronium salt crystallizes out. It is filtered off and is hydrolysed to the benzyl thiol without further purification by treating 1 mole of the benzyl thiouronium salt in a two-necked flask with 300 ml of 5 N caustic sodium carbonate and the mixture is refluxed in a slow current of nitrogen for 2 hours. The cooled reaction mixture is acidified with 2 N hydrochloric acid; the benzyl thiol layer is separated off and dried with the anhydrous magnesium sulfate and the product is fractionated in vacuum under an atmosphere of nitrogen through a Vigreux column b.p. 73°C/10mm, nD=1.5730. The yield of benzyl thiol is 70%.

Organicum. Practical Handbook of Organic Chemistry, by Heinz Becker, Werner Berger and Günter Domschke, Addison-Wesley Pub. Co, 217-218, (1973)

IUPAC Name

phenylmethanethiol

InChI

InChI=1S/C7H8S/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2

InChI Key

UENWRTRMUIOCKN-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C(C=C1)CS

Depositor-Supplied Synonyms

BENZYL MERCAPTAN, Benzenemethanethiol, Phenylmethanethiol, 100-53-8, Benzylthiol, alpha-Toluenethiol, Thiobenzyl alcohol, Benzylmercaptan, Benzylhydrosulfide, (Mercaptomethyl)benzene, Benzyl hydrosulfide, Phenylmethyl mercaptan, Methanethiol, phenyl-, alpha-Toluolthiol, Toluene-alpha-thiol, alpha-Mercaptotoluene, .alpha.-Toluenethiol, alpha-Tolyl mercaptan, phenyl-methanethiol, USAF ex-1509, .alpha.-Toluolthiol, .alpha.-Mercaptotoluene, .alpha.-Tolyl mercaptan, Toluene, alpha-mercapto-, NSC 41897, FEMA No. 2147, CCRIS 9101, CHEMBL1224557, HSDB 2105, UENWRTRMUIOCKN-UHFFFAOYSA-N, EINECS 202-862-5, BRN 0605864, AI3-22955, benzyl thiol, phenyl methanethiol, benzyl-MERCAPTAN, Thiol, polymer-bound, PubChem6835, Usaf ek-1509, AC1Q7GOO, phenyl-[35S]methanethiol, Alpha-Toluenethiol, 99%, DSSTox_CID_6664, SCHEMBL205, UNII-OS34A21OBZ, WLN: SH1R, AC1L1OX7, ACMC-1C3L0, DSSTox_RID_78178, OS34A21OBZ, DSSTox_GSID_26664, B25401_ALDRICH, Mercaptomethyl, polymer-bound, KSC176I3L, 63767_ALDRICH, W214701_ALDRICH, DODEOYL BENZYL MERCAPTAN, 589985_ALDRICH, 13540_FLUKA, 63767_FLUKA, CTK0H6435, MolPort-001-756-847, EBD43071, NSC41897, ZINC3873647, Tox21_200129, ANW-14314, AR-1H9696, BDBM50325566, DNC011145, NSC-41897, NSC229567, STL299685, ZINC03873647, AKOS000120383, LS-2580, MCULE-9652039678, NSC-229567, RP19608, RTR-032988, TRA0001998, NCGC00248534-01, NCGC00257683-01, AN-24554, CAS-100-53-8, CJ-11004, KB-75436, OR025061, OR192678, OR228661, DB-003602, TR-032988, FT-0622824, LT03333266, 113778-EP2274983A1, 113778-EP2298772A1, 4-06-00-02632 (Beilstein Handbook Reference), I01-0779, Q-100020, 3B3-034773, InChI=1/C7H8S/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H, alpha-Toluenethiol; Benzenemethanethiol; Thiobenzyl alcohol; Toluene-a-thiol, 16528-58-8, 5374-12-9

Removed Synonyms

(Mercaptomethyl)polystyrene, CID7509, c0895, T0287, 10102-94-0

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