1,3-Propanedithiol
Names | |
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IUPAC name
Propane-1,3-dithiol
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Other names
1,3-dimercaptopropane
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Identifiers | |
109-80-8 | |
ChEBI | CHEBI:44864 |
ChEMBL | ChEMBL1235209 |
ChemSpider | 13848090 |
Jmol 3D model | Interactive image |
RTECS number | TZ2585500 |
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Properties | |
C3H8S2 | |
Molar mass | 108.22 g·mol−1 |
Appearance | Colorless liquid |
Density | 1.078 g/cm3 |
Melting point | −79 °C (−110 °F; 194 K) |
Boiling point | 169 °C (336 °F; 442 K) |
slight | |
Solubility in solvents | all organic solvents |
Refractive index (nD)
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1.539 |
Structure | |
0 D | |
Vapor pressure | {{{value}}} |
Related compounds | |
Related compounds
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1,2-ethanedithiol 1,2-propanedithiol lipoic acid |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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verify (what is ?) | |
Infobox 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.
Use in organic synthesis
1,3-Propanedithiol is mainly used for the protection of aldehydes and ketones via their reversible formation of dithianes.[1] A prototypical reaction is its formation of 1,3-dithiane from formaldehyde.[2] The reactivity of this dithiane illustrates the concept of umpolung.
The unpleasant odour of 1,3-propanedithiol has encouraged the development of alternative reagents that generate similar derivatives.[3]
Use in inorganic synthesis
1,3-Propanedithiol reacts with metal ions to form chelate rings. Illustrative is the synthesis of the derivative diiron propanedithiolate hexacarbonyl upon reaction with triiron dodecacarbonyl:[4]
- Fe3(CO)12 + C3H6(SH)2 → Fe2(S2C3H6)(CO)6 + H2 + Fe(CO)5 + CO
Safety
The stench of 1,3-propanedithiol can be neutralized with bleach.
See also
References
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