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Triphenylphosphine sulfide

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Triphenylphosphine sulfide
Names
Preferred IUPAC name Triphenyl-λ-phosphanethione
Other names
  • Triphenylphosphane sulfide
  • Triphenylphosphine sulfide
  • Triphenylthioxophosphorane
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.021.280 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C18H15PS/c20-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15HKey: VYNGFCUGSYEOOZ-UHFFFAOYSA-N
  • InChI=1/C18H15PS/c20-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15HKey: VYNGFCUGSYEOOZ-UHFFFAOYAH
SMILES
  • c1ccc(cc1)P(=S)(c2ccccc2)c3ccccc3
Properties
Chemical formula (C6H5)3PS
Molar mass 294.350461 g/mol
Appearance Colourless solid
Melting point 161 to 163 °C (322 to 325 °F; 434 to 436 K)
Solubility soluble in dichloromethane, ethanol
Related compounds
Related compounds Triphenylphosphine oxide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Triphenylphosphine sulfide (IUPAC name: triphenyl-λ-phosphanethione) is the organophosphorus compound with the formula (C6H5)3PS, usually written Ph3PS (where Ph = phenyl). It is a colourless solid, which is soluble in a variety of organic solvents.

Structurally, the molecule resembles the corresponding oxide, with idealized C3 point group symmetry. It is weakly nucleophilic at the sulfur atom.

Applications

Organic synthesis

Triphenylphosphine sulfide is useful for the conversion of epoxides to the corresponding episulfides:

Ph2C2H2O + Ph3PS → Ph2C2H2S + Ph3PO

It also reacts with ketenes to form thioketenes:

Ph2CCO + Ph3PS → Ph2CCS + 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, such as organic trisulfides, react with triphenylphosphine to give Ph3PS, which can be detected by gas chromatography.

References

  1. Codding, P. W.; Kerr, K. A. (1978). "Triphenylphosphine sulfide". Acta Crystallographica Section B. 34 (12): 3785. Bibcode:1978AcCrB..34.3785C. doi:10.1107/S0567740878012212.
  2. Mayhew, Darrin L.; Clive, Derrick L. J. (Apr 15, 2001). "Triphenylphosphine Sulfide". Encyclopedia of Reagents for Organic Synthesis. New York, NY: John Wiley. doi:10.1002/047084289X.rt379. ISBN 0-471-93623-5.
  3. Staudinger, H.; Meyer, Jules (1919). "Über neue organische Phosphorverbindungen III. Phosphinmethylenderivate und Phosphinimine". Helvetica Chimica Acta. 2 (1): 635–646. doi:10.1002/hlca.19190020164. ISSN 0018-019X.
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