(2-Bromophenyl)diphenylphosphine 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 formula (CHBr)P(CH). It is a white crystalline solid that is soluble in nonpolar organic solvents. The compound is used as a precursor to the 2-lithiated derivative of

triphenylphosphine Triphenylphosphine (IUPAC name: triphenylphosphane) is a common organophosphorus compound with the formula P(C6H5)3 and often abbreviated to P Ph3 or Ph3P. It is versatile compound that is widely used as a reagent in organic synthesis and as a l ...

, which in turn is a precursor to other

phosphine ligand A metal-phosphine complex is a coordination complex containing one or more phosphine ligands. Almost always, the phosphine is an organophosphine of the type R3P (R = alkyl, aryl). Metal phosphine complexes are useful in homogeneous catalysis. Prom ...

Preparation

The compound has been prepared by several methods. An efficient route is the coupling reaction of

diphenylphosphine Diphenylphosphine, also known as diphenylphosphane, is an organophosphorus compound with the formula (C6H5)2PH. This foul-smelling, colorless liquid is easily oxidized in air. It is a precursor to organophosphorus ligands for use as catalysts. Syn ...

and 2-bromoiodobenzene, which is catalyzed by palladium complexes (Ph = CH): :CHBr(I) + HPPh + EtN → PhP(CHBr) + tNH The compound is

isomorphous In mathematics, an isomorphism is a structure-preserving mapping or morphism between two structures of the same type that can be reversed by an inverse mapping. Two mathematical structures are isomorphic if an isomorphism exists between them. ...

with (2-tolyl)diphenylphosphine. Lithiation with

butyl lithium Butyllithium may refer to one of 5 isomeric organolithium reagents of which 3 are commonly used in chemical synthesis: * ''n''-Butyllithium, abbreviated BuLi or nBuLi * ''sec''-Butyllithium, abbreviated ''sec''-BuLi or sBuLi, has 2 stereoisomers, ...

gives o-lithiated triphenylphosphine. The bromide also forms a

Grignard reagent Grignard reagents or Grignard compounds are chemical compounds with the general formula , where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride and phenylmagnesium bromi ...

. These metallated phosphines are versatile reagents.Hartley, J. G., Venanzi, L. M., Goodall, D. C., "The preparation and complex-forming properties of one tritertiary and one tetratertiary phosphine", J. Chem. Soc. 1963, 3930. :BrC₆H₄PPh₂ + Mg → BrMgC₆H₄PPh₂ :2 BrMgC₆H₄PPh₂ + PhPCl₂ → PhP ₆H₄PPh₂sub>2 + 2 MgClBr

References

{{DEFAULTSORT:Bromophenyl)diphenylphosphine, (2- Tertiary phosphines Phenyl compounds 2-Bromophenyl compounds