Triphenylphosphine sulfide
Triphenylphosphine sulfide | |
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IUPAC name Triphenyl-λ5-phosphanethione | |
Triphenyl-λ5-phosphanethione | |
Other names Triphenylthioxophosphorane | |
Identifiers | |
CAS number | 3878-45-3 |
PubChem | 19758 |
ChemSpider | 18610 |
Jmol-3D images | Image 1 |
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Properties | |
Molecular formula | C18H15PS |
Molar mass | 294.350461 g/mol |
Appearance | white solid |
Melting point | 161-163 °C |
Solubility in water | dichloromethane, ethanol |
Related compounds | |
Related compounds | Triphenylphosphine oxide |
(verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
Infobox references | |
Triphenylphosphine sulfide (IUPAC name: Triphenyl-λ5-phosphanethione) is the organophosphorus compound with the formula (C6H5)3PS, usually written Ph3PS (Ph = phenyl). It is a colourless solid, which is soluble in a variety of organic solvents.
Structurally, the molecule resemble the corresponding oxide, with ideallized C3v point group symmetry.[1] It is weakly nucleophilic at sulfur.
Applications
Organic synthesis
Triphenylphosphine sulfide is useful for the conversion of epoxides to the corresponding episulfides:[2]
- Ph2C2H2O + Ph3PS → Ph2C2H2S + Ph3PO
Analytical chemistry
In analytical chemistry, triphenylphosphine is used for the analysis of certain kinds of sulfur compounds. Elemental sulfur (S8), as occurs in some oils, and labile organosulfur compounds, e.g. organic trisulfides, react with triphenylphosphine to give Ph3PS, which can be detected by gas chromatography.
References
- ↑ Codding, P. W.; Kerr, K. A. (1978). "Triphenylphosphine sulfide". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry 34 (12): 3785. doi:10.1107/S0567740878012212.
- ↑ Darrin, L. Mayhew, Derrick L. J. Clive, "Triphenylphosphine Sulfide" in Encyclopedia of Reagents for Organic Synthesis, John Wiley, 2001, New York.doi:10.1002/047084289X.rt379 Article Online Posting Date: April 15, 2001