Triphenyl phosphite

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.

Triphenyl phosphite
Names
IUPAC name
Triphenyl phosphite
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.645
UNII
Properties
C18H15O3P
Molar mass 310.28 g/mol
Appearance colourless liquid
Density 1.184 g/mL
Melting point 22 to 24 °C (72 to 75 °F; 295 to 297 K)
Boiling point 360 °C (680 °F; 633 K)
low
Solubility organic solvents
-183.7·10−6 cm3/mol
Hazards
Main hazards flammable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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

Triphenylphosphite is a notable example of polyamorphism in organic compounds, namely it exists in two different amorphous forms at temperatures about 200 K.[2] Not long ago a new long-awaited polymorphic modification of triphenyl phosphite was obtained by means of crystallization in ionic liquids[3]

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 (melting point 147 °C) can be prepared from the nickel(0) complex of cycloocta-1,5-diene:[4]

Ni(COD)2 + 4 P(OC6H5)3 → Ni[P(OC6H5)3]4 + 2 COD

It also forms a variety of Fe(0) and Fe(II) complexes such as the dihydride H2Fe[P(OC6H5)3]4.[5]

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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. Ha, Alice; Cohen, Itai; Zhao, Xiaolin; Lee, Michelle; Kivelson, Daniel (1996). "Supercooled Liquids and Polyamorphism†". The Journal of Physical Chemistry. 100: 1–4. doi:10.1021/jp9530820.
  3. D.G. Golovanov, K.A. Lyssenko, M.Yu. Antipin, Ya.S. Vygodskii, E.I. Lozinskaya, A.S. Shaplov. ”Long-awaited polymorphic modification of triphenyl phosphite“, Cryst. Eng. Comm., 2005, v. 7, no. 77, P.465 – 468. doi: 10.1039/b505052a
  4. 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
  5. Gerlach, D. H.; Peet, W. G.; Muetterties, E. L. (1972). "Stereochemically nonrigid six-coordinate molecules. II. Preparations and reactions of tetrakis(organophosphorus)metal dihydride complexes". Journal of the American Chemical Society. 94 (13): 4545. doi:10.1021/ja00768a022.
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