Synthesis of 2-butanethiol

Preparation of  2-butanethiol

Preparation of 2-butanethiol

Preparation of 2-butanethiol

In a round-bottomed flask, 1 mole of 2-butyl bromide or 2-butyl chloride (or 1/2 mole of 2-dibutyl sulfate) 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 2-butylthiouronium salt crystallizes out. It is filtered off and is hydrolysed to the butyl thiol without further purification by treating 1 mole of the butyl thiouronium salt (in the case of a thiouronium sulfate only 1/2 mole) 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 butyl thiol layer is separated off and dried with the anhydrous magnesium sulfate and the product is fractionated through a Vigreux column b.p. 85°C, nD=1338. The yield of 2-butanethiol is 60%.

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

IUPAC Name

butane-2-thiol

InChI

InChI=1S/C4H10S/c1-3-4(2)5/h4-5H,3H2,1-2H3

InChI Key

LOCHFZBWPCLPAN-UHFFFAOYSA-N

Canonical SMILES

CCC(C)S

Depositor-Supplied Synonyms

2-Butanethiol, SEC-BUTYL MERCAPTAN, 513-53-1, sec-Butyl thiol, 2-Butyl mercaptan, sec-Butanethiol, 2-Mercaptobutane, butane-2-thiol, 1-Methyl-1-propanethiol, sec-Butyl thioalcohol, secondary Butylmercaptan, LOCHFZBWPCLPAN-UHFFFAOYSA-N, NSC 78417, 91840-99-2, 2-Butylmercaptan, 2-Butylthiol, sec-butylmercaptan, 1-methylpropanethiol, sec-C4H9SH, sec.-Butyl thioalcohol, (+-)-2-Butanethiol, AC1L1VGM, sec-Butyl hydrosulfide #, DSSTox_CID_21396, DSSTox_RID_79712, 1-methyl-1-propyl mercaptan, DSSTox_GSID_41396, KSC269S1F, W509434_ALDRICH, 102911_ALDRICH, CHEMBL3183438, CTK1G9912, HSDB 1610, MolPort-003-925-756, NSC78417, EINECS 208-165-2, Tox21_301086, NSC-78417, AKOS000120417, AKOS017278348, RP18544, TRA0028198, NCGC00248283-01, NCGC00254987-01, AN-23500, CAS-513-53-1, OR035339, OR130151, OR372833, U540, DB-021135, KB-169161, RT-000604, B0686, FT-0628765, FT-0657876, I09-0139

Removed Synonyms

Mercaptan C4, CID10560

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