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1,3-propanedithiol
Sign in to saveAlso known as 1,3-propanedimercaptan, trimethylenedithiol, trimethylenedithioglycol, trimethylene dimercaptan, 1,3-dimercaptopropane, dithiotrimethyleneglycol
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.
Chemical data
- Formula
- C3H8S2
- Molecular weight
- 108.23 g/mol
- IUPAC name
- propane-1,3-dithiol
- SMILES
- C(CS)CS
- InChIKey
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N
- XLogP
- 1.2
- Polar surface area
- 2 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 108.007
Show 5 more facts
- chemical formula
- C₃H₈S₂
- canonical SMILES
- C(CS)CS
- Commons category
- Propane-1,3-dithiol
- melting point
- -79.0
- boiling point
- 172.9
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
4 sectionsContents
- Reactions
- Safety
- See also
- References
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.
Excerpted from Wikipedia’s “1,3-propanedithiol” article, available under the CC BY-SA 4.0 licence.