Synthesis of 1,3-propanedithiol

Preparation of 1,3-propanedithiol

Preparation of 1,3-propanedithiol

Preparation of 1,3-propanedithiol

In a round-bottomed flask, 1 mole of 1,3-dibromopropane or 1,3-dichloropropane is added to 2.2 mole of thiourea and 100 ml of 95% alcohol, and the mixture is refluxed for 6 hours. On cooling, the thiouronium salt crystallizes out. It is filtered off and is hydrolysed to the 1,3-propanedithiol without further purification by treating 1 mole of the thiouronium salt in a two-necked flask with 600 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 1,3-propanedithiol 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. 57°C/12mm, nD=1.540. The yield of 1-butanethiol 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

propane-1,3-dithiol

InChI

InChI=1S/C3H8S2/c4-2-1-3-5/h4-5H,1-3H2

InChI Key

ZJLMKPKYJBQJNH-UHFFFAOYSA-N

Canonical SMILES

C(CS)CS

MeSH Synonyms

1,3-propanedithiol

Depositor-Supplied Synonyms

1,3-Propanedithiol, 1,3-DIMERCAPTOPROPANE, Propane-1,3-dithiol, 109-80-8, Trimethylene dimercaptan, Dithiotrimethyleneglycol, Trimethylenedithiol, Trimethylenedithioglycol, 1,3-Propanedimercaptan, NDR-132, UNII-R4LUJ82U52, FEMA No. 3588, ZJLMKPKYJBQJNH-UHFFFAOYSA-N, EINECS 203-706-9, BRN 1071197, 1,3-propandithiol, 1,3 propanedithiol, Trimethylene Dithiol, 1,3-propane dithiol, 1,3-propane-dithiol, propane 1,3-dithiol, 1,3-Propyldimercaptan, ACMC-1BUS9, AC1L1Q2C, SCHEMBL25497, P50609_ALDRICH, KSC175E5T, W358800_ALDRICH, R4LUJ82U52, CHEBI:44864, CTK0H5259, MolPort-003-939-167, EBD31056, ZINC3860693, ANW-16092, ZINC03860693, AKOS009031264, RL00421, RP18906, RTR-002088, TRA0008346, AN-42964, CJ-10876, KB-10462, OR010894, SC-17571, DB-003157, LS-120787, TR-002088, FT-0606744, FT-0625200, P0763, AZ0001-0477, 51375-EP2292597A1, 51375-EP2305808A1, 51375-EP2311824A1, 103976-EP2302015A1, 4-01-00-02503 (Beilstein Handbook Reference), A802090, 3B4-1220, I09-0008, Q-100053, InChI=1/C3H8S2/c4-2-1-3-5/h4-5H,1-3H, Trimethylene dimercaptan; 1,3-Propanedithiol; Propane-1,3-dithiol

Removed Synonyms

Dithiol deriv., CID8013, AIDS081871, PDT

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