Triphenyl phosphite

From Wikipedia, the free encyclopedia

Triphenyl phosphite
IUPAC name Triphenyl phosphite
Identifiers
CAS number [101-02-0]
PubChem 24889800
Properties
Molecular formula C18H15O3P
Molar mass 310.28 g/mol
Appearance colourless liquid
Density 1.184 g/mL
Melting point

22-24 °C
Boiling point

360 °C
Solubility in water organic solvents
Hazards
Main hazards flammable
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

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:[1]

3 CH3MgBr + P(OC6H5)3 → P(CH3)3 + 3 MgBrOC6H5

[edit] 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:[2]

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.[3]

[edit] References

  1. ^ 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
  2. ^ 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,
  3. ^ 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