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
References



![1,3-Propanedithiol: Structure of (C3H6S2)2, the oxidized "dimer" of 1,3-propanedithiol.[4]](https://upload.wikimedia.org/wikipedia/commons/thumb/9/9d/CSD_CIF_CANHEE.png/330px-CSD_CIF_CANHEE.png?utm_source=en.wikipedia.org&utm_campaign=parser&utm_content=thumbnail)
