Triethyl phosphite

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:[1] In the absence of the base, the reaction of ethanol and phosphorus trichloride affords diethylphosphite ((EtO)2P(O)H).[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.Its complexes are generally lipophilic and feature metals in low oxidation states.
Michaelis–Arbuzov reaction between ethyl bromoacetate and triethyl phosphite resulting in an organophosphonate.
Michaelis–Arbuzov reaction between ethyl bromoacetate and triethyl phosphite resulting in an organophosphonate.
Reaction scheme and proposed mechanism for carbonyl α-hydroxylation using oxygen and triethyl phosphite.
Reaction scheme and proposed mechanism for carbonyl α-hydroxylation using oxygen and triethyl phosphite .
Preferred IUPAC nameCAS NumberChemSpiderECHA InfoCardPubChemCompTox DashboardSMILESChemical formulaMolar massDensityMelting pointBoiling pointSolubilityMagnetic susceptibilityOccupational safety and healthstandard stateorganophosphorus compoundphosphite esterformulaligandorganometallic chemistryorganic synthesisphosphorus trichlorideethanoldiethylphosphiteMichaelis–Arbuzov reactionethyl bromoacetateHorner–Wadsworth–Emmons reactionhydroperoxidesCorey–Winter olefin synthesiscoordination chemistryhomogeneous catalysiscopper(I) iodideInorganic Syntheses