Triphenylphosphine sulfide

Triphenylphosphine sulfide
Names
	IUPAC names Triphenyl-λ5-phosphanethione; Triphenylphosphane sulfide; Triphenylphosphine sulfide
	Preferred IUPAC name Triphenyl-λ5-phosphanethione
	Other names Triphenylthioxophosphorane
Identifiers
CAS Number	3878-45-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	18610 ;
ECHA InfoCard	100.021.280
PubChem CID	19758;
CompTox Dashboard (EPA)	DTXSID10192046 ;
	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/h1-15H Key: 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/h1-15H Key: VYNGFCUGSYEOOZ-UHFFFAOYAH;
	SMILES c1ccc(cc1)P(=S)(c2ccccc2)c3ccccc3;
Properties
Chemical formula	C18H15PS
Molar mass	294.350461 g/mol
Appearance	white solid
Melting point	161 to 163 °C (322 to 325 °F; 434 to 436 K)
Solubility in water	dichloromethane, ethanol
Related compounds
Related compounds	Triphenylphosphine oxide
	Except where otherwise noted, 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 (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 C_3v point group symmetry.[1] It is weakly nucleophilic at the sulfur atom.

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

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References

Codding, P. W.; Kerr, K. A. (1978). "Triphenylphosphine sulfide". Acta Crystallographica Section B. 34 (12): 3785. doi:10.1107/S0567740878012212.
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.

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[1] Codding, P. W.; Kerr, K. A. (1978). "Triphenylphosphine sulfide". Acta Crystallographica Section B. 34 (12): 3785. 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.