Synthesis of isobutyl mercaptan

Preparation of isobutyl mercaptan

Preparation of isobutyl mercaptan

Preparation of isobutyl mercaptan

In a round-bottomed flask, 1 mole of isobutyl bromide or isobutyl chloride (or 1/2 mole of diisobutyl 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 isobutyl thiouronium salt crystallizes out. It is filtered off and is hydrolysed to the isobutyl thiol without further purification by treating 1 mole of the isobutyl  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 isobutyl thiol layer is separated off and dried with the anhydrous magnesium sulfate and the product is fractionated through a Vigreux column b.p. 88°C, nD=14358. The yield of isobutyl mercaptan is 55%.

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

IUPAC Name

2-methylpropane-1-thiol

InChI

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

InChI Key

BDFAOUQQXJIZDG-UHFFFAOYSA-N

Canonical SMILES

CC(C)CS

Depositor-Supplied Synonyms

Isobutyl mercaptan, 2-METHYL-1-PROPANETHIOL, Isobutylmercaptan, 2-Methylpropane-1-thiol, 513-44-0, Isobutanethiol, 1-Propanethiol, 2-methyl-, BDFAOUQQXJIZDG-UHFFFAOYSA-N, EINECS 208-162-6, BRN 1730890, iso-butyl thiol, 1-Isobutanethiol, 2-methylpropanethiol, 2-Methyl propanethiol, 2-methyl-propanethiol, iso-C4H9SH, ACMC-1AOZD, 2-Methyl-1-propylthiol, AC1L1VGG, 2-methyl-propane-1-thiol, 1-Propanethiol,2-methyl-, UNII-9H070UFP2X, KSC491I1B, W387401_ALDRICH, 112917_ALDRICH, 9H070UFP2X, BDFAOUQQXJIZDG-UHFFFAOYSA-, CTK3J1410, MolPort-003-925-949, LTBB003933, ZINC5008005, ANW-31242, ZINC05008005, AKOS000120213, MCULE-7978911055, RTR-018298, TRA0065805, AN-23498, CJ-12384, KB-52731, OR035340, OR276127, LS-121038, TR-018298, FT-0612909, FT-0652457, M0404, 4-01-00-01605 (Beilstein Handbook Reference), A828544, I09-0140, InChI=1/C4H10S/c1-4(2)3-5/h4-5H,3H2,1-2H3

Removed Synonyms

Isobutyl thiol, CID10558

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