1,3-Propanedithiol is the chemical compound with the formula HSCH2CH2CH2SH. This dithiol is a useful reagent in organic synthesis. This liquid, which is readily available commercially, has an intense stench.
Reactions 1,3-Propanedithiol has been used for the protection of aldehydes and ketones via their reversible formation of dithianes. A prototypical reaction is its formation of 1,3-dithiane from formaldehyde. The reactivity of this dithiane illustrates the concept of umpolung. Alkylation gives thioethers, e.g. 1,5-dithiacyclooctane. The unpleasant odour of 1,3-propanedithiol has encouraged the development of alternative reagents that generate similar derivatives.
Oxidation gives not the 1,2-dithiolane, but the bis(disulfide).
1,3-Propanedithiol is used in the synthesis of tiapamil.
1,3-Propanedithiol reacts with metal ions to form dithiolates. Illustrative is the synthesis of the derivative diiron propanedithiolate hexacarbonyl upon reaction with triiron dodecacarbonyl: Fe3(CO)12 + C3H6(SH)2 → Fe2(S2C3H6)(CO)6 + H2 + Fe(CO)5 + CO
Safety The stench of 1,3-propanedithiol can be minimized with bleach.
See also 1,2-Propanedithiol
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