Triethyl phosphite
Encyclopedia
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:
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).
, 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).
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....
P(OCH2CH3)3, often abbreviated P(OEt)3. This colorless liquid is used as a ligand
Ligand
In coordination chemistry, a ligand is an ion or molecule that binds to a central metal atom to form a coordination complex. The bonding between metal and ligand generally involves formal donation of one or more of the ligand's electron pairs. The nature of metal-ligand bonding can range from...
in organometallic chemistry
Organometallic chemistry
Organometallic chemistry is the study of chemical compounds containing bonds between carbon and a metal. Since many compounds without such bonds are chemically similar, an alternative may be compounds containing metal-element bonds of a largely covalent character...
and as a reagent in organic synthesis
Organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...
. The molecule features a pyramidal phosphorus(III) center bound to three ethoxide groups.
Triethylphosphite is prepared by treating phosphorus trichloride
Phosphorus trichloride
Phosphorus trichloride is a chemical compound of phosphorus and chlorine, having chemical formula PCl3. Its shape is trigonal pyramidal. It is the most important of the three phosphorus chlorides. It is an important industrial chemical, being used for the manufacture of organophosphorus compounds...
with ethanol
Ethanol
Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...
in the presence of a base, typically a tertiary amine:
- 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 catalysisHomogeneous catalysis
In chemistry, homogeneous catalysis is a sequence of reactions that involve a catalyst in the same phase as the reactants. Most commonly, a homogeneous catalyst is codissolved in a solvent with the reactants.-Acid 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).