Triethylphosphite

Triethylphosphite

Names
IUPAC name Triethyl phosphite
Other names Triethoxyphosphine
Identifiers
CAS Number	122-52-1 Y
3D model (Jmol)	Interactive image
ChemSpider	28956 Y
ECHA InfoCard	100.004.139
PubChem CID	31215
InChI InChI=1S/C6H15O3P/c1-4-7-10(8-5-2)9-6-3/h4-6H2,1-3H3 Y Key: BDZBKCUKTQZUTL-UHFFFAOYSA-N Y InChI=1/C6H15O3P/c1-4-7-10(8-5-2)9-6-3/h4-6H2,1-3H3 Key: BDZBKCUKTQZUTL-UHFFFAOYAP
SMILES O(P(OCC)OCC)CC
Properties
Chemical formula	C6H15O3P
Molar mass	166.16 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 in water	organic solvents
Magnetic susceptibility (χ)	-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).
Y  (what is YN ?)
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. 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:

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).

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).