Triethyl phosphite
| Names | |
|---|---|
| Preferred IUPAC name
Triethyl phosphite | |
| Other names
Triethoxyphosphine | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.004.139 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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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 their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references | |
Triethyl phosphite (TEP) is an organophosphorus compound, specifically a phosphite ester, with the formula P(OCH2CH3)3, often abbreviated P(OEt)3. It is a colorless, malodorous liquid. It 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. Its 31P NMR spectrum features a signal at around +139 ppm vs phosphoric acid standard.
Triethylphosphite is prepared by treating phosphorus trichloride with ethanol in the presence of a base, typically a tertiary amine:
- PCl3 + 3 EtOH + 3 R3N → P(OEt)3 + 3 R3NH + 3 Cl−
In the absence of the base, the reaction of ethanol and phosphorus trichloride affords diethylphosphite ((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).