Phenylphosphine is an

organophosphorus compound Organophosphorus compounds are organic compounds containing phosphorus. They are used primarily in pest control as an alternative to chlorinated hydrocarbons that persist in the environment. Some organophosphorus compounds are highly effective in ...

with the chemical formula C₆H₅PH₂. It is the phosphorus analog of

aniline Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine In organic chemistry, an aromatic amine is an organic compound consisting of an aroma ...

. 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 (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 electr ...

coordination chemistry A coordination complex consists of a central atom or ion, which is usually metallic and is called the ''coordination centre'', and a surrounding array of bound molecules or ions, that are in turn known as ''ligands'' or complexing agents. Many ...

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: :LiAlH₄ + 2C₆H₅PCl₂ → 2C₆H₅PH₂ + Li⁺ + Al³⁺ + 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 , where R is the rest of the molecule. It consists of a methylene bridge () attached to a vinyl group (). The name is derived from the scientific name for garlic, ...

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 Phosphinidenes (IUPAC: phosphanylidenes, formerly phosphinediyls) are low-valent phosphorus compounds analogous to carbenes and nitrenes, having the general structure RP. The "free" form of these compounds is conventionally described as having a si ...

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