Phenylcopper
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3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C6H5Cu | |
| Molar mass | 140.652 g·mol−1 |
| Appearance | Colorless crystals |
| reacts with water | |
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Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Phenylcopper is an organometallic chemical compound of copper.[1] Its chemical formula is C6H5Cu,[2] where copper is in the oxidation state of +1.
Synthesis
[edit | edit source]Phenylcopper was the first known organocopper compound and was first prepared in 1923 from phenylmagnesium iodide and copper(I) iodide and in 1936 by Henry Gilman by transmetallation of phenylmagnesium iodide with copper(I) chloride.
Phenylcopper can be obtained by reacting phenyl lithium with copper(I) bromide in diethyl ether.[3]
- C6H5Li + CuBr → C6H5Cu + LiBr
Properties
[edit | edit source]Phenylcopper is a colorless solid that is soluble in pyridine. It can be stored for a few days without decomposition under nitrogen or in vacuum. Rapid decomposition takes place in air. Water decomposes phenylcopper to form red copper(I) oxide and varying amounts of benzene and biphenyl. It forms stable complexes with tributylphosphine and triphenylphosphine.[4]
When dissolved in dimethyl sulfide, phenylcopper forms dimers and trimers (aggregates of two or three molecules).[5]
Related structures
[edit | edit source]A diphenylcuprate(I) ion exists that can form a salt with lithium (lithium diphenylcuprate(I) Li+[Cu(C6H5)2]−),[5] an example of a Gilman reagent.
References
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