1,3-Propanedithiol
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| 1,3-Propanedithiol | |
|---|---|
| Image:H2pdt.png | |
| IUPAC name | 1,3-Propanedithiol |
| Other names | 1,3-dimercaptopropane |
| Identifiers | |
| CAS number | |
| 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 | |
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 from formaldehyde.[1] 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.[1]
Use in inorganic synthesis
1,3-Propanedithiol reacts with metal ions to form chelate rings. Illustrative is the synthesis of the diiron derivative:[1]
Safety
The stench of 1,3-propanedithiol can be neutralized with bleach.
See also
References
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
