Copper(I) acetate
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CAS Number
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.009.036 |
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PubChem CID
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CompTox Dashboard (EPA)
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InChI
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| Properties[1] | |
Chemical formula
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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) |
Solubility in water
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hydrolyzes forming Cu2O |
| Solubility | soluble in pyridine, acetic acid dissolves slowly in ether |
| Structure[2] | |
Crystal structure
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monoclinic |
Space group
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P21/m (No. 11) |
Lattice constant
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a = 5.221 Å, b = 6.259 Å, c = 9.928 Å α = 90°, β = 93.63°, γ = 90°
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| Hazards | |
| GHS labelling:[3] | |
Pictograms
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Signal word
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Warning |
Hazard statements
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H315, H319, H335 |
Precautionary statements
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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).
Infobox references
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Copper(I) acetate (cuprous acetate) is an organic copper salt of acetic acid with chemical formula CH3COOCu. It is an air-sensitive white solid.
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]
References
- ^ a b c Parish, Edward J.; Kizito, Stephen A. (2001-04-15), John Wiley & Sons, Ltd (ed.), "Copper(I) Acetate", Encyclopedia of Reagents for Organic Synthesis, Chichester, UK: John Wiley & Sons, Ltd, doi:10.1002/047084289X.rc193, ISBN 978-0-471-93623-7, retrieved 2026-02-17
{{citation}}: CS1 maint: work parameter with ISBN (link) - ^ a b Mounts, Richard D.; Ogura, Tetsuya.; Fernando, Quintus. (1974-04-01). "Crystal structure of copper(I) acetate". Inorganic Chemistry. 13 (4): 802–805. doi:10.1021/ic50134a008. ISSN 0020-1669. Retrieved 2025-06-29.
- ^ "Copper(I) acetate". pubchem.ncbi.nlm.nih.gov.
- ^ Shao, Changwei; Cheng, Guolin; Su, Deyong; Xu, Jimin; Wang, Xinyan; Hu, Yuefei (2010-07-05). "Copper(I) Acetate: A Structurally Simple but Highly Efficient Dinuclear Catalyst for Copper‐Catalyzed Azide‐Alkyne Cycloaddition". Advanced Synthesis & Catalysis. 352 (10): 1587–1592. doi:10.1002/adsc.200900768. ISSN 1615-4150.
- ^ Lewin, Anita H.; Goldberg, Norman L. (1972-01-01). "Organocopper species III. The reaction of copper (I) carboxylates with organyl halides". Tetrahedron Letters. 13 (6): 491–492. doi:10.1016/S0040-4039(01)84358-6. ISSN 0040-4039.
- ^ Edwards, Dennis A.; Richards, Roger (1975-01-01). "Complexes of copper(I) acetate. Part I. Complexes with σ-donor ligands". Journal of the Chemical Society, Dalton Transactions (7): 637–643. doi:10.1039/DT9750000637. ISSN 1364-5447.