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Dichlorophenylphosphine is an 
Reductive coupling of the dichlorophosphine gives 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 ...
C6H5PCl2. This colourless viscous liquid is commonly used in the synthesis of organophosphine
Organophosphines are organophosphorus compounds with the formula PR''n''H3−''n'', where R is an organic substituent. These compounds can be classified according to the value of ''n'': primary phosphines (''n'' = 1), secondary phosphin ...
s.
Dichlorophenylphosphine is commercially available. It may be prepared by an electrophilic substitution
Electrophilic substitution reactions are chemical reactions in which an electrophile displaces a functional group in a compound, which is typically, but not always, aromatic. Aromatic substitution reactions are characteristic of aromatic compounds ...
of benzene
Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...
by 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 ...
, catalyzed by aluminium chloride
Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula . It forms a hexahydrate with the formula , containing six water molecules of hydration. Both the anhydrous form and the hexahydrate are col ...
. However, aluminum chloride
Aluminium chloride, also known as aluminium trichloride, is an inorganic compound with the formula . It forms a hexahydrate with the formula , containing six water molecules of hydration. Both the anhydrous form and the hexahydrate are col ...
often induces diarylation; a cleaner catalyst for monoarylation is stannic chloride
Tin(IV) chloride, also known as tin tetrachloride or stannic chloride, is an inorganic compound of tin and chlorine with the formula SnCl4. It is a colorless hygroscopic liquid, which fumes on contact with air. It is used as a precursor to other t ...
. The compound is an intermediate for the synthesis of other chemicals for instance dimethylphenylphosphine
Dimethylphenylphosphine is an organophosphorus compound with a formula P(C6H5)(CH3)2. The phosphorus is connected to a phenyl group and two methyl groups, making it the simplest aromatic alkylphosphine. It is colorless air sensitive liquid. It i ...
:
:C6H5PCl2 + 2 CH3MgI → C6H5P(CH3)2 + 2 MgICl
Many tertiary phosphines can be prepared by this route.
In the McCormack reaction
The McCormack reaction is a method for the synthesis of organophosphorus compounds. In this reaction, a 1,3-diene and a source of R2P+ are combined to give phospholenium cation. The reaction is named after W. B. McCormack, a research chemist at duP ...
dichlorophenylphosphine adds diene
In organic chemistry, a diene ( ); also diolefin, ) or alkadiene) is a covalent compound that contains two double bonds, usually among carbon atoms. They thus contain two alk''ene'' units, with the standard prefix ''di'' of systematic nome ...
s to give the chlorophospholenium ring.
:
Reductive coupling of the dichlorophosphine gives the cyclophosphine
Cyclopentaphosphine is the inorganic compound with the formula . It is prepared by the hydrolysis of cyclo-. Although only of theoretical interest, is parent of many related cyclic polyphosphines that are the subject of research.
Organic cyclo ...
(PhP)5.{{cite journal , author = Marianne Baudler, Klaus Glinka , title = Monocyclic and Polycyclic Phosphines , journal = Chem. Rev. , year = 1993 , volume = 93 , pages = 1623–1667 , doi = 10.1021/cr00020a010
References