Triethyl phosphite
Names | |
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Preferred IUPAC name
Triethyl phosphite | |
Other names
Triethoxyphosphine
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Identifiers | |
3D model (
JSmol ) |
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ChemSpider | |
ECHA InfoCard
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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
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toxic |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Triethyl phosphite is an
The molecule features a pyramidal phosphorus(III) center bound to three ethoxide groups. Its 31P
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 + 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).
Reactions
Triethyl phosphite can react with electrophiles in a Michaelis–Arbuzov reaction to produce organophosphonates. For example, the reaction between triethyl phosphite and ethyl bromoacetate produces a phosphonate suitable for use in the Horner–Wadsworth–Emmons reaction.[2]
Reduction/deoxygenation of hydroperoxides 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 the Corey–Winter olefin synthesis.[2]
As a ligand
In
References
- .
- ^ ISBN 0-471-93623-5.
- PMID 5742870.
- PMID 24281892.
- ISBN 978-0-470-13259-3.