Synthesis of 1-dodecanethiol

Preparation of  1-dodecanethiol

Preparation of 1-dodecanethiol

Preparation of 1-dodecanethiol

In a round-bottomed flask, 1 mole of dodecane bromide or dodecane chloride (or 1/2 mole of didodecane 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 dodecanethiouronium salt crystallizes out. It is filtered off and is hydrolysed to the dodecane thiol without further purification by treating 1 mole of the dodecane 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 dodecane 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. 154°C/20mm, nD=1.4575. The yield of 1-dodecanethiol 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

dodecane-1-thiol

InChI

InChI=1S/C12H26S/c1-2-3-4-5-6-7-8-9-10-11-12-13/h13H,2-12H2,1H3

InChI Key

WNAHIZMDSQCWRP-UHFFFAOYSA-N

Canonical SMILES

CCCCCCCCCCCCS

MeSH Synonyms

1-dodecanethiol, dodecylmercaptan

Depositor-Supplied Synonyms

1-DODECANETHIOL, Dodecane-1-thiol, Dodecyl mercaptan, Lauryl mercaptan, 112-55-0, n-Dodecanethiol, n-Dodecyl mercaptan, Dodecanethiol, N-Dodecylmercaptan, 1-Mercaptododecane, n-Lauryl mercaptan, 1-Dodecyl mercaptan, Dodecylmercaptan, Pennfloat M, Pennfloat S, Lauryl mercaptide, M-Lauryl mercaptan, M-Dodecyl mercaptan, NSC 814, NCI-C60935, Dodecyl mercaptan (VAN), UNII-S8ZJB6X253, CCRIS 743, HSDB 1074, WNAHIZMDSQCWRP-UHFFFAOYSA-N, EINECS 203-984-1, SBB060132, BRN 0969337, AI3-07577, DSSTox_CID_5220, DSSTox_RID_77706, DSSTox_GSID_25220, Tris(dodecylthio)antimony, 1322-36-7, CAS-112-55-0, 1-Dodecanethiol, antimony(3+) salt, laurylmercaptan, Dodecylthiol, dodecane thiol, n-Dodecylthiol, 1-dodecanthiol, 1-dodecylthiol, dodecyl-mercaptan, 1-dodecylmercaptan, Mercaptan C12, n-dodecyl-mercaptan, Dodecanethiol-(1), ACMC-1CUIY, AC1L1QHA, SCHEMBL15369, KSC175O0F, 471364_ALDRICH, AC1Q2W78, NSC814, S8ZJB6X253, Jsp000967, CHEMBL3185403, CTK0H5702, NSC-814, MolPort-001-780-209, NSC11884, Tox21_201758, Tox21_303101, ANW-16489, AR-1C2759, LS-555, MFCD00004885, NSC-11884, NSC229570, STL483072, ZINC59144932, WLN: 12S-SB-S12&S12, AKOS015960383, MCULE-8388213802, NSC-229570, RL00505, RTR-002449, TRA-0205507, NCGC00249113-01, NCGC00257179-01, NCGC00259307-01, AN-22708, BP-10739, KB-12050, LP001689, SC-19063, DB-021314, TR-002449, D0970, FT-0607709, FT-0693266, FT-0694976, ST51046367, J-504580, S14-1460, 3B3-033401, InChI=1/C12H26S/c1-2-3-4-5-6-7-8-9-10-11-12-13/h13H,2-12H2,1H, 30237-11-7

Removed Synonyms

tert-Dodecyl mercaptan, Stibine, tris(dodecylthio)-, CID8195, Thioantimonic acid (H3SbS3), tridodecyl ester, 4-01-00-01851 (Beilstein Handbook Reference), 25103-58-6, NDM, 6939-83-9, 7148-54-1

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