Triphenyl phosphite

Triphenyl phosphite

Names
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
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	organic solvents
Magnetic susceptibility (χ)	-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).
N  (what is YN ?)
Infobox 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:

Trimethylphosphine is prepared from triphenylphosphite:

Triphenylphosphite 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

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:

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