Triphenyl phosphite

Triphenyl phosphite
Names
	IUPAC name Triphenyl phosphite
Identifiers
CAS Number	101-02-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	7259 ;
ECHA InfoCard	100.002.645
PubChem CID	7540;
UNII	9P45GRD24X ;
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 Key: HVLLSGMXQDNUAL-UHFFFAOYSA-N ; 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). verify (what is ?) 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:

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 1,5-cyclooctadiene:^[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]

References

^ 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
^ 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.
^ 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
^ 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,
^ 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.

[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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