Triethyl phosphite

Triethyl phosphite is an organophosphorus compound 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

Triethyl phosphite
Names
IUPAC name
Triethyl phosphite
Other names
Triethoxyphosphine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.139
UNII
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)
organic solvents
-104.8·10−6 cm3/mol
Hazards
Main hazards 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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Infobox references

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]

PCl3 + 3 EtOH + 3 R3N → P(OEt)3 + 3 R3NH + Cl−

In the absence of the base, the reaction 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).

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. 108 °C).[2]

References
  1. Ford-Moore, A. H.; Perry, B. J. (1951). "Triethyl Phosphite". Org. Synth. 31: 111. doi:10.15227/orgsyn.031.0111.
  2. Ittel, Steven D. (1990). "Complexes of Nickel(0)". Inorganic Syntheses. 28: 98–104. doi:10.1002/9780470132593.ch26. ISBN 978-0-470-13259-3.
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