Triethyl phosphite

Triethyl phosphite
Names
	IUPAC name Triethyl phosphite
	Other names Triethoxyphosphine
Identifiers
CAS Number	122-52-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	28956 ;
ECHA InfoCard	100.004.139
PubChem CID	31215;
UNII	6B2R04S55G ;
CompTox Dashboard (EPA)	DTXSID2026991 ;
	InChI InChI=1S/C6H15O3P/c1-4-7-10(8-5-2)9-6-3/h4-6H2,1-3H3 Key: BDZBKCUKTQZUTL-UHFFFAOYSA-N ; 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	166.157 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)
Solubility in water	organic solvents
Magnetic susceptibility (χ)	-104.8·10−6 cm3/mol
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	toxic
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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

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. 187 °C).^[2]

References

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

External links

WebBook page for C6H15PO3

[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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