Triphenylphosphine sulfide

Names
Preferred IUPAC name

Triphenyl-λ5-phosphanethione

Other names

* Triphenylphosphane sulfide
* Triphenylphosphine sulfide
* Triphenylthioxophosphorane

Identifiers

CAS Number

* 3878-45-3 N

3D model (JSmol)

* Interactive image

ChemSpider |

* 18610 Y

PubChem CID

* 19758

UNII |

* Q68E5JRQ8V Y

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 Y

Key: VYNGFCUGSYEOOZ-UHFFFAOYSA-N Y

* 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

| (C

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 [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Triphenylphosphine sulfide (IUPAC name: triphenyl-λ5-phosphanethione) is the organophosphorus compound with the formula (C

3PS, usually written Ph
3PS (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.[1] It is weakly nucleophilic at the sulfur atom.

## Contents

* 1 Applications
* 1.1 Organic synthesis
* 1.2 Analytical chemistry
* 2 References

## Applications

### Organic synthesis

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

2O + Ph
3PS → Ph

2S + Ph
3PO

### Analytical chemistry

In analytical chemistry, triphenylphosphine is used for the analysis of certain kinds of sulfur compounds. Elemental sulfur (S
8), as occurs in some oils, and labile organosulfur compounds, such as organic trisulfides, react with triphenylphosphine to give Ph
3PS, 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. 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.

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*[CID]: Compound ID