Triphenylphosphine

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Triphenylphosphine
Names
IUPAC name
Triphenylphosphane
Other names
TPP
Properties
C18H15P
P(C6H5)3
PPh3
Ph3P
Molar mass 262.292 g/mol
Appearance White solid
Odor Nearly odorless
Density 1.194 g/cm3 (at 20 °C)
Melting point 80 °C (176 °F; 353 K)
Boiling point 377 °C (711 °F; 650 K)
0.0017 g/100 ml (at 22 °C)
Solubility Soluble in glacial acetic acid, benzene, CCl4, chloroform, diethyl ether, THF
Slightly soluble in alcohols
Vapor pressure 1.1·10-4 mmHg
Acidity (pKa) 7.64 (pKa of conjugate acid in acetonitrile)
Hazards
Safety data sheet Sigma-Aldrich
Flash point 180 °C (356 °F; 453 K)
Lethal dose or concentration (LD, LC):
700 mg/kg (rat, oral)
Related compounds
Related compounds
Phosphine
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 - often abbreviated to PPh3 or Ph3P.

Properties

Chemical

Triphenylphosphine is a weak base, but does form stable salts with strong acids such as HCl and HBr.

Triphenylphosphine undergoes slow oxidation by air to give triphenylphosphine oxide, Ph3PO:

2 PPh3 + O2 → 2 Ph3PO

Triphenylphosphine abstracts sulfur from polysulfide compounds, episulfides, and elemental sulfur, forming triphenylphosphine sulfide, Ph3PS. Simple organosulfur compounds such as thiols and thioethers are unreactive, however.

Physical

Triphenylphosphine is a white solid,

Availability

Triphenylphosphine is sold by lab suppliers.

Preparation

Can be made by reacting phosphorus trichloride with phenylmagnesium bromide or phenyllithium.

Projects

  • Make triphenylphosphine oxide
  • Make PPh3 complexes ([Co(PPh3)2]Cl2 e.g.)

Handling

Safety

Triphenylphosphine is irritant.

Storage

In closed plastic or glass bottles, away from oxidizers.

Disposal

Controlled oxidation/incineration will suffice.

References

Relevant Sciencemadness threads