Triethyl phosphite

Triethyl phosphite
Identifiers
CAS number 122-52-1 Y
PubChem 31215
ChemSpider 28956 Y
Jmol-3D images Image 1
Properties
Molecular formula C6H15O3P
Molar mass 166.16 g/mol
Appearance colorless liquid
Density 0.969 g/mL
Melting point

-70 °C, 203 K, -94 °F

Boiling point

156 °C (57–58 °C/16 mm)

Solubility in water organic solvents
Hazards
Main hazards toxic
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Triethylphosphite is an organophosphorus compound with the formula P(OCH2CH3)3, often abbreviated P(OEt)3. This colorless liquid 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.

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-

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. 187 °C).[2]

References

  1. ^ A. H. Ford-Moore and B. J. Perry (1963), "Triethyl Phosphite", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV4P0955 ; Coll. Vol. 4: 955 
  2. ^ Ittel, Steven D.; Berke, H.; Dietrich, H.; Lambrecht, J.; Hrter, P.; Opitz, J.; Springer, W. (1990). "Complexes of Nickel(0)". Inorganic Syntheses. Inorganic Syntheses 28: 98–104. doi:10.1002/9780470132593.ch26. ISBN 9780470132593. 

External links