Triphenyl phosphite

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ImageFile = P(OPh)3.png ImageSize = 200px
IUPACName = Triphenyl phosphite
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Section1 = Chembox Identifiers
CASNo = 101-02-0
PubChem = 24889800
SMILES =
Section2 = Chembox Properties
Formula = C₁₈H₁₅O₃P
MolarMass = 310.28 g/mol
Appearance = colourless liquid
Density = 1.184 g/mL
MeltingPt = 22-24 °C
BoilingPt = 360 °C
Solubility = organic solvents
Section3 = Chembox Hazards
MainHazards = flammable
FlashPt =
Autoignition =

Triphenyl phosphite is the chemical compound with the formula P(OC₆H₅)₃. This colourless viscous liquid is the ester of phosphorous acid and phenol. It is used as a ligand in organometallic chemistry. Nickel complexes of this ligand are homogeneous catalysts for the hydrocyanation of alkenes.

Triphenylphosphite is prepared from phosphorus trichloride and phenol in the presence of a base::PCl₃ + 3 HOC₆H₅ → P(OC₆H₅)₃ + 3 HCl

Trimethylphosphine is prepared from triphenylphosphite: [Leutkens, Jr., M. L.; Sattelberger, A. P.; Murray, H. H.; Basil, J. D.; Fackler, Jr., J. P. "Trimethylphosphine" Inorganic Syntheses, 1990, volume 28, pages 305-310. ISBN 0-471-52619-3] : 3 CH₃MgBr + P(OC₆H₅)₃ → P(CH₃)₃ + 3 MgBrOC₆H₅

Representative coordination complexes

Triphenylphosphite forms zero-valent complexes of the type M [P(OC₆H₅)₃] ₄ for M = Ni, Pd, Pt. The colourless nickel complex (m.p. 147 °C) can be prepared from the nickel(0) complex of 1,5-cyclooctadiene: [Ittel, S. D. "Olefin, Acetylene, Phosphine, Isocyanide, and Diazene Complexes of Nickel(0)" Inorganic Syntheses, 1977, volume XVII, p. 117-124. ISBN 0-07-044327-0,] : Ni(COD)₂ + 4 P(OC₆H₅)₃ → Ni [P(OC₆H₅)₃] ₄ + 2 COD

It also forms a variety of Fe(O) and Fe(II) complexes such as the dihydride H₂Fe [P(OC₆H₅)₃] ₄. [Gerlach, D. H.; Peet, W. G. and Muetterties, E. L., "Stereochemically nonrigid six-coordinate molecules. II. Preparations and reactions of tetrakis(organophosphorus)metal dihydride complexes", Journal of the American Chemical Societry, 1972, volume 94, pp 4545-9.DOI: 10.1021/ja00768a022]

References