Triphenylphosphine sulfide

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Triphenylphosphine sulfide
Triphenylphosphine-sulfide-2D-skeletal.png
Triphenylphosphine-sulfide-3D-balls.png
Identifiers
CAS number 3878-45-3 N
PubChem 19758
ChemSpider 18610 YesY
Jmol-3D images Image 1
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
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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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[edit]

Organic synthesis[edit]

Triphenylphosphine sulfide is useful for the conversion of epoxides to the corresponding episulfides:[2]

Ph2C2H2O + Ph3PS → Ph2C2H2S + Ph3PO

Analytical chemistry[edit]

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[edit]

  1. ^ 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. 
  2. ^ 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