Appearance colourless liquid | ||
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Triphenyl phosphite 99 min cas no 101 02 0
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.
Contents
Triphenylphosphite is prepared from phosphorus trichloride and phenol in the presence of a base:
PCl3 + 3 HOC6H5 → P(OC6H5)3 + 3 HClTrimethylphosphine is prepared from triphenylphosphite:
3 CH3MgBr + P(OC6H5)3 → P(CH3)3 + 3 MgBrOC6H5Triphenylphosphite is a notable example of polyamorphism in organic compounds, namely it exists in two different amorphous forms at temperatures about 200 K. Not long ago a new long-awaited polymorphic modification of triphenyl phosphite was obtained by means of crystallization in ionic liquids
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 1,5-cyclooctadiene:
Ni(COD)2 + 4 P(OC6H5)3 → Ni[P(OC6H5)3]4 + 2 CODIt also forms a variety of Fe(0) and Fe(II) complexes such as the dihydride H2Fe[P(OC6H5)3]4.