Triphenyl phosphite

Triphenyl phosphite is the organophosphorus compound with the formula P(OC₆H₅)₃. It is a colourless viscous liquid.

Triphenyl phosphite

Names
Preferred IUPAC name Triphenyl phosphite
Identifiers
CAS Number	101-02-0 Y
3D model (JSmol)	Interactive image
ChemSpider	7259 Y
ECHA InfoCard	100.002.645
PubChem CID	7540
UNII	9P45GRD24X N
CompTox Dashboard (EPA)	DTXSID0026252
InChI InChI=1S/C18H15O3P/c1-4-10-16(11-5-1)19-22(20-17-12-6-2-7-13-17)21-18-14-8-3-9-15-18/h1-15H Y Key: HVLLSGMXQDNUAL-UHFFFAOYSA-N Y InChI=1/C18H15O3P/c1-4-10-16(11-5-1)19-22(20-17-12-6-2-7-13-17)21-18-14-8-3-9-15-18/h1-15H Key: HVLLSGMXQDNUAL-UHFFFAOYAF
SMILES O(P(Oc1ccccc1)Oc2ccccc2)c3ccccc3
Properties
Chemical formula	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)
Solubility in water	low
Solubility	organic solvents
Magnetic susceptibility (χ)	−183.7·10−6 cm3/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	flammable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Preparation

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

Reactions

Triphenylphosphite is a precursor to trimethylphosphine, it serves as a source of P³⁺ that is less electrophilic than phosphorus trichloride:^[1]

(C₆H₅O)₃P + 3 CH₃MgBr → P(CH₃)₃ + 3 "MgBrOC₆H₅"

Triphenylphosphite is quaternized by methyl iodide:^[2]

(C₆H₅O)₃P + CH₃I → [CH₃(C₆H₅O)₃P]⁺I⁻

Coordination complexes

Triphenylphosphite is a common ligand in coordination chemistry. It forms zero-valent complexes of the type M[P(OC₆H₅)₃]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(OC₆H₅)₃]₄ + 2 COD

Related 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(OC₆H₅)₃]₄.^[4]

Polyamorphism

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]