Triphenyl phosphite is the
organophosphorus compound
Organophosphorus chemistry is the scientific study of the synthesis and properties of organophosphorus compounds, which are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbo ...
with the
formula
In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...
P(OC
6H
5)
3. It is a colourless viscous liquid.
Preparation
Triphenylphosphite is prepared from
phosphorus trichloride
Phosphorus trichloride is an inorganic compound with the chemical formula PCl3. A colorless liquid when pure, it is an important industrial chemical, being used for the manufacture of phosphites and other organophosphorus compounds. It is toxic ...
and
phenol
Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire.
The molecule consists of a phenyl group () ...
in the presence of a catalytic amount of base:
:PCl
3 + 3 HOC
6H
5 → P(OC
6H
5)
3 + 3 HCl
Reactions
Triphenylphosphite is a precursor to
trimethylphosphine, it serves as a source of P
3+ that is less electrophilic than phosphorus trichloride:
: (C
6H
5O)
3P + 3CH
3MgBr → P(CH
3)
3 + 3"MgBrOC
6H
5"
Triphenylphosphite is quaternized by
methyl iodide
Iodomethane, also called methyl iodide, and commonly abbreviated "MeI", is the chemical compound with the formula CH3I. It is a dense, colorless, volatile liquid. In terms of chemical structure, it is related to methane by replacement of one h ...
:
: (C
6H
5O)
3P + CH
3I →
H3(C6H5O)3Psup>+I
−
Coordination complexes
Triphenylphosphite is a common
ligand
In coordination chemistry, a ligand is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's el ...
in
coordination chemistry
A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of chemical bond, bound molecules or ions, that are in turn known as ' ...
. It forms zero-valent complexes of the type M
(OC6H5)3sub>4 (M = Ni, Pd, Pt). The nickel complex can be prepared by displacement of the diene from
bis(cyclooctadiene)nickel:
: Ni(COD)
2 + 4 P(OC
6H
5)
3 → Ni
(OC6H5)3sub>4 + 2 COD
Related complexes are
homogeneous catalysts for the
hydrocyanation of
alkene
In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as Alpha-olefin, α-olefins.
The Internationa ...
s. It also forms a variety of Fe(0) and Fe(II) complexes such as the di
hydride
In chemistry, a hydride is formally the anion of hydrogen (H−), a hydrogen ion with two electrons. In modern usage, this is typically only used for ionic bonds, but it is sometimes (and has been more frequently in the past) applied to all che ...
H
2Fe
(OC6H5)3sub>4.
Polyamorphism
Triphenylphosphite is a notable example of
polyamorphism
Polyamorphism is the ability of a substance to exist in several different amorphous modifications. It is analogous to the polymorphism of crystalline materials. Many amorphous substances can exist with different amorphous characteristics (e.g. ...
in organic compounds, namely it exists in two different amorphous forms at temperatures about 200 K. One polymorphic modification of triphenyl phosphite was obtained by means of crystallization in
ionic liquid
An ionic liquid (IL) is a salt (chemistry), salt in the liquid state at ambient conditions. In some contexts, the term has been restricted to salts whose melting point is below a specific temperature, such as . While ordinary liquids such as wate ...
s.
[D.G. Golovanov, K.A. Lyssenko, M.Yu. Antipin, Ya.S. Vygodskii, E.I. Lozinskaya, A.S. Shaplov. ”Long-awaited polymorphic modification of triphenyl phosphite“, Cryst. Eng. Comm., 2005, v. 7, no. 77, P.465 – 468]
doi: 10.1039/b505052a
/ref>
References
{{reflist
Phenol ethers
Organophosphites