Phenylphosphine is an
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 chemical formula C
6H
5PH
2. It is the phosphorus analog of
aniline
Aniline (From , meaning ' indigo shrub', and ''-ine'' indicating a derived substance) is an organic compound with the formula . Consisting of a phenyl group () attached to an amino group (), aniline is the simplest aromatic amine. It is an in ...
. Like other
primary phosphines, phenylphosphine has an intense penetrating odor and is highly oxidizable. It is mainly used as a precursor to other organophosphorus compounds. It can function as a
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 ' ...
.
Synthesis
Phenylphosphine can be produced by reducing
dichlorophenylphosphine
Dichlorophenylphosphine is an organophosphorus compound with the formula C6H5PCl2. This colourless viscous liquid is commonly used in the synthesis of organophosphines.
Dichlorophenylphosphine is commercially available. It may be prepared by an ...
with lithium aluminum hydride in ether:
:LiAlH
4 + 2C
6H
5PCl
2 → 2C
6H
5PH
2 + Li
+ + Al
3+ + 4Cl
−
This reaction is performed under a
nitrogen atmosphere to prevent side reactions involving oxygen.
Reactions
Oxidation of phenylphosphine with air affords the oxide.
[
:C6H5PH2 + O2 → C6H5P(OH)2
Bis(2-cyanoethylphenyl)phosphine, which is of interest as a synthetic intermediate, can be made from phenylphosphine by base-catalyzed ]allyl
In organic chemistry, an allyl group is a substituent with the structural formula . It consists of a methylene bridge () attached to a vinyl group (). The name is derived from the scientific name for garlic, . In 1844, Theodor Wertheim isolated a ...
ic addition to acrylonitrile.
:C6H5PH2 + 2CH2=CHCN → C6H5P(CH2CH2CN)2
Bis(2-cyanoethylphenyl)phosphine is a useful precursor to 1-phenyl-4-phosphorinanone by base-induced cyclization followed by hydrolysis. Phosphorinanones can be used to prepare alkenes, amines, indoles, and secondary and tertiary alcohols by reduction, Grignard, and Reformatsky reagents.
Phenylphosphine reacts with many metal complexes to give complexes and clusters. It is the precursor to the bridging phosphinidene ligand in certain clusters.
:2 (C6H5)2MCl + C6H5PH2 + 3 (C2H5)3N → ((C6H5)2M)2PC6H5 + 3 (C2H5)3N•HCl
Phenylphosphine also have uses in polymer synthesis. Using radical initiations or UV irradiation, polyaddition of phenylphosphine to 1,4-divinylbenzene or 1,4-diisopropenylbenzene will form phosphorus-containing polymers, which have self-extinguishing properties. When mixed with flammable polymers such as polystyrene and polyethylene, the mixed polymer exhibits flame resistant properties.
References
{{Reflist
Phosphines
Foul-smelling chemicals