Triethyl phosphite

Triethyl phosphite

Chembox new
ImageFile=P(OEt)3.pngImageSize=200px
IUPACName=Triethyl phosphite
OtherNames= Triethoxyphosphine
Section1= Chembox Identifiers
CASNo=122-52-1
PubChem=24900347
SMILES=

Section2= Chembox Properties
Formula=C6H15O3P
MolarMass=166.16
Appearance=colorless liquid
Density=0.969
MeltingPtC=-70
BoilingPt=156°C (57–58°C/16 mm)
Solubility=organic solvents

Section3= Chembox Hazards
MainHazards=toxic
FlashPt=
Autoignition=

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: [OrgSynth | author = A. H. Ford-Moore and B. J. Perry | title = Triethyl Phosphite | collvol = 4 | collvolpages = 955 | year = 1963 | prep = CV4P0955] :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). [cite journal | last = Ittel | first = Steven D. | year = 1990 | title = Complexes of Nickel(0) | journal = Inorganic Syntheses | volume = 28 | pages = 98–104 | doi = 10.1002/9780470132593.ch26]

References

External links

* [http://webbook.nist.gov/cgi/cbook.cgi?ID=C122521 WebBook page for C6H15PO3]


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