1,3-Propanedithiol is used as a reagent in the preparation of thioketals and thioacetals. It acts as a flavoring agent. It is used as a precursor in the synthesis of cyclic dithioacetal (1,3-dithiane) derivatives of carbonyl compounds. It is involved in the preparation of diiron propanedithiolate hexacarbonyl by reacting reaction with triiron dodecacarbonyl. Further, it is used for the protection of aldehydes and ketones through their reversible formation of dithianes. In addition to this, it reacts with metal ions to form chelate rings.
Precursor of cyclic dithioacetal (1,3-dithiane) derivatives of carbonyl compounds. The protection step is catalyzed by Lewis acids, e.g. BF3 etherate: Tetrahedron Lett., 871 (1971), TiCl4: Tetrahedron Lett., 24, 1289 (1983), Aluminum trifluoromethanesulfonate, B20785, or Indium(III) trifluoromethanesulfonate, 40131. Diothioacetalization can be accomplished under neutral, solvent-free conditions using Lithium trifluoromethanesulfonate, 39322, as catalyst: Tetrahedron Lett., 40, 4055 (1999). For the preparation of monocyclic dithioacetals of ß-diketones at low temperature in the presence of BF3 etherate, see: Tetrahedron, 44, 2283 (1988).
Alternatively, 1,3-dithianes can be prepared by alkylation with reactive gem-dihalides under phase-transfer conditions: Liebigs Ann. Chem., 1589 (1982).
For deprotection methods and uses of 1,3-dithianes as acyl anion equivalents, see: 1,3-Dithiane, A10505.
Wang, L.; Li, R.; Feng, L.; Liu, J.; Gao, X.; Wang, W. Study on the interface electronic states of chemically modified ZnO nanowires. RSC Adv. 2015, 5 (119), 98130-98135.
Kuciński, K.; Pawlu?, P.; Marciniec, B.; Hreczycho, G. Highly Selective Hydrothiolation of Unsaturated Organosilicon Compounds Catalyzed by Scandium(III) Triflate. Chem. Eur. J. 2015, 21 (13), 4940-4943.
Gefahrenhinweise (EU): H227-H315-H319-H335
Combustible liquid. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
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