Triphenyl phosphite is the organophosphorus compound with the formula P(OC6H5)3. It is a colourless viscous liquid.
Triphenylphosphite is prepared from phosphorus trichloride and phenol in the presence of a catalytic amount of base:
PCl3 + 3 HOC6H5 → P(OC6H5)3 + 3 HCl
Triphenylphosphite is a precursor to trimethylphosphine, it serves as a source of P3+ that is less electrophilic than phosphorus trichloride:[1]
(C6H5O)3P + 3CH3MgBr → P(CH3)3 + 3"MgBrOC6H5"
Triphenylphosphite is quaternized by methyl iodide:[2]
(C6H5O)3P + CH3I → [CH<sub>3</sub>(C<sub>6</sub>H<sub>5</sub>O)<sub>3</sub>P]+I−
Triphenylphosphite is a common ligand in coordination chemistry. It forms zero-valent complexes of the type M[P(OC<sub>6</sub>H<sub>5</sub>)<sub>3</sub>]4 (M = Ni, Pd, Pt). The nickel complex can be prepared by displacement of the diene from bis(cyclooctadiene)nickel:[3]
Ni(COD)2 + 4 P(OC6H5)3 → Ni[P(OC<sub>6</sub>H<sub>5</sub>)<sub>3</sub>]4 + 2 CODRelated complexes are homogeneous catalysts for the hydrocyanation of alkenes. It also forms a variety of Fe(0) and Fe(II) complexes such as the dihydride H2Fe[P(OC<sub>6</sub>H<sub>5</sub>)<sub>3</sub>]4.[4]
Triphenylphosphite is a notable example of polyamorphism in organic compounds, namely it exists in two different amorphous forms at temperatures about 200 K.[5] One polymorphic modification of triphenyl phosphite was obtained by means of crystallization in ionic liquids.[6]