Triphenyl phosphite
| Triphenyl phosphite | |
|---|---|
| File:P(OPh)3.png | |
| File:TriphenylPhosphite 3D BallStick.png | |
| Triphenyl phosphite | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 101-02-0 
|
| PubChem | 24889800 |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C18H15O3P |
| Molar mass | 310.28 g/mol |
| Appearance | colourless liquid |
| Density | 1.184 g/mL |
| Melting point |
22–24 °C |
| Boiling point |
360 °C |
| Solubility in water | organic solvents |
| style="background: #F8EABA; text-align: center;" colspan="2" | Hazards | |
| Main hazards | flammable |
 (what is this?) (verify)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| 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]
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 (m.p. 147 °C) can be prepared from the nickel(0) complex of 1,5-cyclooctadiene:[3]
- Ni(COD)2 + 4 P(OC6H5)3 → Ni[P(OC6H5)3]4 + 2 COD
It also forms a variety of Fe(O) and Fe(II) complexes such as the dihydride H2Fe[P(OC6H5)3]4.[4]
References
Cite error: Invalid <references> tag;
parameter "group" is allowed only.
<references />, or <references group="..." />- ↑ 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. doi:10.1021/jp9530820.
- ↑ 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: 4545. doi:10.1021/ja00768a022.
3.png){kind=link}
