Copper(I) acetate
Chemical compound
From Wikipedia, the free encyclopedia
Copper(I) acetate (cuprous acetate) is an organic copper salt of acetic acid with chemical formula CH3COOCu. It is an air-sensitive white solid.
| Identifiers | |
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3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.009.036 |
| EC Number |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties[1] | |
| C2H3CuO2 | |
| Molar mass | 122.590 g·mol−1 |
| Appearance | tan or white solid |
| Density | 2.52 g/cm3 |
| Melting point | 285 °C (545 °F; 558 K) (decomposes) |
| hydrolyzes forming Cu2O | |
| Solubility | soluble in pyridine, acetic acid dissolves slowly in ether |
| Structure[2] | |
| monoclinic | |
| P21/m (No. 11) | |
a = 5.221 Å, b = 6.259 Å, c = 9.928 Å α = 90°, β = 93.63°, γ = 90° | |
| Hazards | |
| GHS labelling:[3] | |
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| Warning | |
| H315, H319, H335 | |
| P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
Copper(I) acetate is produced by the reduction of anhydrous copper(II) acetate with copper metal in acetonitrile or pyridine.[2] The reaction is performed under vacuum to prevent oxidation of the product.
It can also be prepared by treating copper(I) oxide with an acetic acid–acetic anhydride solution.[1]
Uses
Copper(I) acetate is used as a catalyst for the oxidation of phenols to the corresponding poly-(phenylene) ethers and diphenoquinones in the presence of tertiary amines.[1]
It also catalyzes azide-alkyne cycloaddition reactions.[4]
Reactions
Copper(I) acetate reacts with primary, secondary, tertiary, allylic and vinylic halides and tosylates yielding the corresponding acetate esters.[5] The reaction is performed in refluxing pyridine, under an inert atmosphere and anhydrous conditions.
It forms complexes with many unidentate and bidentate sigma donor ligands.[6]