Phenylcopper

Phenylcopper is an organometallic chemical compound of copper.^[1] Its chemical formula is C₆H₅Cu,^[2] where copper is in the oxidation state of +1.

Phenylcopper

Names
Other names Copper(1+) benzenide Phenylcopper(I)
Identifiers
CAS Number	3220-49-3 Y
3D model (JSmol)	Interactive image
ChemSpider	13322947
PubChem CID	10997120
CompTox Dashboard (EPA)	DTXSID20451156
InChI InChI=1S/C6H5.Cu/c1-2-4-6-5-3-1;/h1-5H;/q-1;+1 Key: MKHQMLKDCBPKBC-UHFFFAOYSA-N
SMILES C1=CC=[C-]C=C1.[Cu+]
Properties
Chemical formula	C6H5Cu
Molar mass	140.652 g·mol−1
Appearance	Colorless crystals
Solubility in water	reacts with water
Related compounds
Related compounds	Phenyllithium Phenylsodium Phenylsilver
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Synthesis

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

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

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.