Dichlorophenylphosphine
Encyclopedia
Dichlorophenylphosphine is an organophosphorus compound with the formula
C6H5PCl2. This colourless viscous liquid is commonly used in the synthesis of phosphine
ligands.
Dichlorophenylphosphine is commercially available. It may be prepared by a electrophilic substitution
of benzene
by phosphorus trichloride
, catalyzed by aluminium chloride
. The compound is an intermediate for the synthesis of other chemicals for instance dimethylphenylphosphine
:
Dichlorophenylphosphine undergoes the McCormack reaction
upon treatment with diene
s to give phosphole
s.
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....
C6H5PCl2. This colourless viscous liquid is commonly used in the synthesis of phosphine
Phosphine
Phosphine is the compound with the chemical formula PH3. It is a colorless, flammable, toxic gas. Pure phosphine is odourless, but technical grade samples have a highly unpleasant odor like garlic or rotting fish, due to the presence of substituted phosphine and diphosphine...
ligands.
Dichlorophenylphosphine is commercially available. It may be prepared by a electrophilic substitution
Electrophilic substitution
Electrophilic substitution reactions are chemical reactions in which an electrophile displaces a group in a compound, typically but not always hydrogen. Electrophilic aromatic substitution is characteristic of aromatic compounds and is an important way of introducing functional groups onto benzene...
of benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....
by 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...
, catalyzed by aluminium chloride
Aluminium chloride
Aluminium chloride is the main compound of aluminium and chlorine. It is white, but samples are often contaminated with iron trichloride, giving it a yellow colour. The solid has a low melting and boiling point. It is mainly produced and consumed in the production of aluminium metal, but large...
. The compound is an intermediate for the synthesis of other chemicals for instance dimethylphenylphosphine
Dimethylphenylphosphine
Dimethylphenylphosphine is a organophosphorus compound with a formula P2. The phosphorus is connected to a phenyl group and two methyl groups. This colorless air sensitive liquid is commonly used as a ligand in transition metal complexes...
:
- C6H5PCl2 + 2 CH3MgI → C6H5P(CH3)2 + 2 MgICl
Dichlorophenylphosphine undergoes the McCormack reaction
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 duPont....
upon treatment with diene
Diene
In organic chemistry a diene or diolefin is a hydrocarbon that contains two carbon double bonds.Conjugated dienes are functional groups, with a general formula of CnH2n-2. Dienes and alkynes are functional isomers...
s to give phosphole
Phosphole
Phosphole is the organic compound with the chemical formula C4H4PH; it is the phosphorus analog of pyrrole. The term phosphole also refers to substituted derivatives of the parent heterocycle...
s.