Triphenyl phosphite
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| Preferred IUPAC name
Triphenyl phosphite | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.002.645 
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| 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) |
| low | |
| Solubility | organic solvents |
| -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). | |
 (what is   ?)
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| Infobox references | |
Triphenyl phosphite is the organophosphorus compound with the formula P(OC6H5)3. It is a colourless viscous liquid.
Preparation[]
Although it can be viewed as the triester of phosphorous acid and phenol, it is not prepared in that way. Instead, triphenylphosphite is prepared from phosphorus trichloride and phenol in the presence of a 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]
References[]
- ^ Leutkens, Jr., M. L.; Sattelberger, A. P.; Murray, H. H.; Basil, J. D.; Fackler, Jr. J. P. (1990). "Trimethylphosphine". Inorganic Syntheses. 28: 305–310. doi:10.1002/9780470132593.ch76.CS1 maint: multiple names: authors list (link)
- ^ H. N. Rydon (1971). "Alkyl Iodides: Neopentyl Iodide and Iodocyclohexane". Organic Syntheses. 51: 44. doi:10.15227/orgsyn.051.0044.
- ^ Ittel, Steven D. (1977). "Olefin, Acetylene, Phosphine, Isocyanide, and Diazene Complexes of Nickel(0)". Inorganic Syntheses. XVII: 117–124. doi:10.1002/9780470132487.ch34.
- ^ 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.
- ^ 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
- Phenol ethers
- Organophosphites