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| Names | |
|---|---|
| Preferred IUPAC name Triethyl phosphite | |
| Other names Triethoxyphosphine | |
| Identifiers | |
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3D model (JSmol) | |
| ChemSpider |
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| ECHA InfoCard | 100.004.139 |
| UNII | |
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| Properties | |
| C6H15O3P | |
| Molar mass | 166.157 g·mol−1 |
| Appearance | colorless liquid |
| Density | 0.969 g/mL |
| Melting point | −70 °C (−94 °F; 203 K) |
| Boiling point | 156 °C (313 °F; 429 K) (57 to 58 °C at 16 mm) |
| Solubility | soluble in most organic solvents |
| -104.8·10−6 cm3/mol | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards | toxic |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Triethyl phosphite (TEP) is anorganophosphorus compound, specifically aphosphite ester, with theformula P(OCH2CH3)3, often abbreviated P(OEt)3. It is a colorless, malodorous liquid. It is used as aligand inorganometallic chemistry and as a reagent inorganic synthesis.
The molecule features a pyramidal phosphorus(III) center bound to three ethoxide groups. Its31PNMR spectrum features a signal at around +139 ppm vs phosphoric acid standard.
Triethylphosphite is prepared by treatingphosphorus trichloride withethanol in the presence of a base, typically a tertiary amine:[1]
In the absence of the base, the reaction of ethanol and phosphorus trichloride affordsdiethylphosphite ((EtO)2P(O)H). 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).
Triethyl phosphite can react with electrophiles in aMichaelis–Arbuzov reaction to produce organophosphonates. For example, the reaction between triethyl phosphite andethyl bromoacetate produces a phosphonate suitable for use in theHorner–Wadsworth–Emmons reaction.[2]
Reduction/deoxygenation ofhydroperoxides to the alcohols can also be effected using triethyl phosphite.[2] This approach can be utilized for carbonyl α-hydroxylation by reacting the enolate with oxygen, producing an α-hydroperoxide which can be reduced by triethyl phosphite to the alcohol.[3] A proposed mechanism is shown below.[4]
Triethyl phosphite can also be used in theCorey–Winter olefin synthesis.[2]
Incoordination chemistry andhomogeneous catalysis, triethylphosphite finds use as asoft 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. 108 °C).[5] It also forms a stable complex withcopper(I) iodide.[2]
