Triphenylphosphine

Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to PPh3 or Ph3P. It is versatile compound that is widely used as a reagent in organic synthesis and as a ligand for transition metal complexes, including ones that serve as catalysts in organometallic chemistry. PPh3 exists as relatively air stable, colorless crystals at room temperature. It dissolves in non-polar organic solvents such as benzene and diethyl ether.

Triphenylphosphine
Names
Preferred IUPAC name
Triphenylphosphane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.009.124
EC Number
  • 210-036-0
RTECS number
  • SZ3500000
UNII
UN number 3077
  • InChI=1S/C18H15P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H Y
    Key: RIOQSEWOXXDEQQ-UHFFFAOYSA-N Y
  • InChI=1/C18H15P/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
    Key: RIOQSEWOXXDEQQ-UHFFFAOYAH
  • c1ccccc1P(c2ccccc2)c3ccccc3
Properties
C18H15P
Molar mass 262.292 g·mol−1
Appearance White Solid
Density 1.1 g cm−3, solid
Melting point 80 °C (176 °F; 353 K)
Boiling point 377 °C (711 °F; 650 K)
Insoluble
Solubility organic solvents
Acidity (pKa) 7.64 (pKa of conjugate acid in acetonitrile)

2.73 (pKa of conjugate acid, aqueous scale)

-166.8·10−6 cm3/mol
1.59; εr, etc.
Structure
Pyramidal
1.4 - 1.44 D
Hazards
GHS labelling:
Danger
H302, H317, H350, H412
P201, P202, P261, P264, P270, P272, P273, P280, P281, P301+P312, P302+P352, P308+P313, P321, P330, P333+P313, P363, P405, P501
NFPA 704 (fire diamond)
2
1
2
Flash point 180 °C (356 °F; 453 K)
Safety data sheet (SDS) Fisher Scientific
Related compounds
Trimethylphosphine
Phosphine
Related compounds
 Triphenylamine
Triphenylarsine
Triphenylstibine
Triphenylphosphine oxide
Triphenylphosphine sulfide
Triphenylphosphine dichloride
Triphenylphosphine selenide
Pd(PPh3)4
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references
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