1,3-Propanedithiol
From Wikipedia, the free encyclopedia
| 1,3-Propanedithiol | |
|---|---|
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| IUPAC name | 1,3-Propanedithiol |
| Other names | 1,3-dimercaptopropane |
| Identifiers | |
| CAS number | [109-80-8] |
| RTECS number | TZ2585500 |
| Properties | |
| Molecular formula | C3H8S |
| Molar mass | 108.23 g/mol |
| Appearance | colourless liquid, stench |
| Density | 1.078 g/cm³ |
| Melting point |
-79 °C |
| Boiling point |
169 °C |
| Solubility in water | slight |
| Solubility in solvents | all organic solvents |
| Refractive index (nD) | 1.539 |
| Structure | |
| Dipole moment | 0 D |
| Hazards | |
| Main hazards | stench |
| R-phrases | 36/37/38 |
| S-phrases | 26 |
| Flash point | 138 °F |
| Related compounds | |
| Related compounds | 1,2-ethanedithiol 1,2-propanedithiol lipoic acid |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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.
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[edit] 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 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]
[edit] Use in inorganic synthesis
1,3-Propanedithiol reacts with metal ions to form chelate rings. Illustrative is the synthesis of the diiron derivative:[4]
[edit] Safety
The stench of 1,3-propanedithiol can be neutralized with bleach.
[edit] See also
[edit] References
- ^ Conrow, R. E.; Le Huérou, Y. (2004). "1,3-Propanedithiol".. J. Wiley & Sons, New York. DOI:10.1002/047084289.
- ^ Corey, E. J.; Seebach, D. (1988). "1,3-Dithiane". Org. Synth.; Coll. Vol. 6: 556.
- ^ Liu, Q.; Che, G. Yu, H.; Liu, Y.; Zhang, J. Zhang, Q.; Dong, D. (2003). "The First Nonthiolic, Odorless 1,3-Propanedithiol Equivalent and Its Application in Thioacetalization". Journal of Organic Chemistry 68: 9148–9150. doi:.
- ^ Winter, A.; Zsolnai, L. and Huttner, G. (1982). "Zweikernige und dreikernige Carbonyleisenkomplexe mit 1,2- und 1,3-Dithiolatobrückenliganden". Zeitschrift für Naturforschung 37b: 1430–1436.
