Triethyl phosphite
From Wikipedia, the free encyclopedia
| Triethyl phosphite | |
|---|---|
3.png/200px-P(OEt)3.png) |
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| IUPAC name | Triethyl phosphite |
| Other names | Triethoxyphosphine |
| Identifiers | |
| CAS number | [122-52-1] |
| PubChem | |
| Properties | |
| Molecular formula | C6H15O3P |
| Molar mass | 166.16 |
| Appearance | colorless liquid |
| Density | 0.969 |
| Melting point |
-70 °C, 203 K, -94 °F |
| Boiling point |
156°C (57–58°C/16 mm) |
| Solubility in water | organic solvents |
| Hazards | |
| Main hazards | toxic |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Triethylphosphite is an organophosphorus compound with the formula P(OCH2CH3)3, often abbreviated P(OEt)3. This colorless liquid is used as a ligand in organometallic chemistry and as a reagent in organic synthesis. The molecule features a pyramidal phosphorus(III) center bound to three ethoxide groups.
Triethylphosphite is prepared by treating phosphorus trichloride with ethanol in the presence of a base, typically a tertiary amine:[1]
- PCl3 + 3 EtOH + 3 R3N → P(OEt)3 + 3 R3NH+Cl-
Of the many related compounds can be prepared similarly, triisopropyl phosphite is an example (b.p. 43.5 °C/1.0 mm; CAS# 116-17-6).
[edit] As a ligand
In coordination chemistry and homogeneous catalysis, triethylphosphite finds use as a soft ligand. Its complexes are generally lipophilic and feature metals in low oxidation states. Examples include the colorless complexes FeH2(P(OEt)3)4 and Ni(P(OEt)3)4 (m.p. 187 °C).[2]
[edit] References
- ^ A. H. Ford-Moore and B. J. Perry (1963). "Triethyl Phosphite". Org. Synth.; Coll. Vol. 4: 955.
- ^ Ittel, Steven D. (1990). "Complexes of Nickel(0)". Inorganic Syntheses 28: 98–104. doi:.
