Copper(I) chloride



Copper(I) chloride
IUPAC name Copper(I) chloride
Other names Cuprous chloride
Identifiers
CAS number 7758-89-6
RTECS number GL6990000
Properties
Molecular formula CuCl
Molar mass 98.99 g/mol
Appearance white powder, slightly
green from oxidation
Density 4.140 g/cm3, solid
Melting point

430 °C (703 K)

Boiling point

1490 °C (1760 K),
decomposes

Solubility in water 0.0062 g/100 ml (20 °C)
Structure
Crystal structure Tetrahedral Zinc blende structure)
Hazards
MSDS ScienceLab.com
Main hazards Irritant
NFPA 704
0
3
0
 
R/S statement R: 22, 50, 53 S: 22, 60/61
Related Compounds
Other anions Copper(I) bromide
Copper(I) iodide
Other cations Copper(II) chloride
Silver(I) chloride
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Copper(I) chloride (quite commonly called cuprous chloride), is the lower aluminum chloride as in the COPureSM process.

In aqueous solution, CuCl would be unstable with respect to solubility.[1]

Chemical properties

Copper(I) chloride is a triphenylphosphine:

CuCl + PPh3 → [CuCl(PPh3)]4 (Ph = phenyl)

Although CuCl is insoluble in water, it dissolves in aqueous solutions containing suitable donor molecules. It readily forms complexes with NH3.

Solutions of CuCl in 1,5-cyclooctadiene are particularly stable:[2]


CuCl reacts with organometallic compounds such as Grignard reagents react similarly.

Preparation

Copper(I) chloride may be prepared by the reduction of copper(II) salts such as copper metal.[3]

2 CuBr2 + H2O + SO32- → 2 CuBr + SO42- + 2 HBr

Le Chatelier's principle).

(1) l)

(2) 2 H2SO4(aq)

(3) HCuCl2(aq) + H3O+(aq) + Cl-(aq)

Uses

A major chemical use for copper(I) chloride is as a catalyst for a variety of organic reactions. Compared to other "soft" Lewis acids, it is much more affordable than non-toxic silver(I) chloride and mercury(II) chloride. In addition, it can undergo redox chemistry via copper(II) or copper(III) intermediates. This combination of properties make copper(I) salts invaluable reagents.

One such application is in the Sandmeyer reaction.[4] Treatment of an arenediazonium salt with CuCl leads to an aryl chloride, for example:


The reaction has wide scope, and usually gives good yields.

The observation that copper(I) halides catalyse 1,4-addition of organic synthesis:[1]


Although other copper(I) compounds such as copper(I) iodide are now more often used for this type of reaction, there are cases where copper(I) chloride is particularly effective:[1]


Here, Bu indicates an n-Grignard reagent alone gives a mixture of 1,2 and 1,4-addition products (i.e., the butyl adds at the closer to the C=O).

Copper(I) chloride is also an intermediate formed from Wacker process.

CuCl is used as a catalyst in Atom Transfer Radical Polymerization (ATRP).

Precautions

Copper salts do have some toxicity and should be handled with care; wear gloves and goggles. Avoid bringing CuCl into contact with alkynes.[6]

References

  1. ^ a b c Greenwood, N.N.; Earnshaw, A. Chemistry of the Elements, 2nd ed., Butterworth-Heinemann, Oxford, UK, 1997.
  2. ^ Nicholls, D. Compleses and First-Row Transition Elements, Macmillan Press, London, 1973.
  3. ^ Keller, R. N.; Wycoff, H. D. "Copper(I) chloride" Inorganic Syntheses 1946; Volume II, p 1-4.
  4. ^ (a) Wade, L. G. Organic Chemistry, 5th ed., p. 871, Prentice Hall, Upper Saddle RIver, New Jersey, 2003. (b) March, J. Advanced Organic Chemistry, 4th ed., p. 723, Wiley, New York, 1992.
  5. ^ Kharasch, M. S.; Tawney, P. O. Journal of the American Chemical Society, 63, 2308 (1941).
  6. ^ Wells, A. F. Structural Inorganic Chemistry, 5th ed., Oxford University Press, Oxford, UK, 1984.
 
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