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{{chembox| Verifiedfields = changed| Watchedfields = changed| verifiedrevid = 451266922| Name = Copper(II) acetate| ImageFile = Copper(II) acetate anhydrous.jpg| ImageCaption = Small crystals of copper(II) acetate| ImageFile1 = Copper(II)-acetate-3D-balls2.png| ImageCaption1 = Copper(II) acetate monohydrate| ImageName1 = Copper(II) acetate hydrate| IUPACName = Tetra-μ2-acetatodiaquadicopper(II)| OtherNames = Copper(II) ethanoateCupric acetateCopper acetateVerdigris| SystematicName = | Section1 = {{Chembox Identifiers

correct|chemspider}}| ChemSpiderID = 8555| PubChem = 8895

correct|FDA}}| UNII1 = 39M11XPH03| UNII1_Comment = (anhydrous)

correct|FDA}}| UNII2 = 39J9V52S86| UNII2_Comment = (hydrate)| EC_number = 205-553-3| UNNumber = 3077| InChI = 1/2C2H4O2.Cu/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2| InChIKey = OPQARKPSCNTWTJ-NUQVWONBAO| SMILES = [O+]1C(C)O[Cu-3]23([OH2+])[O+]C(C)O[Cu-3]1([OH2+])(OC(C)[O+]2)OC(C)[O+]3

correct|chemspider}}| StdInChI = 1S/2C2H4O2.Cu/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2

correct|chemspider}}| StdInChIKey = OPQARKPSCNTWTJ-UHFFFAOYSA-L

correct|CAS}}| CASNo = 142-71-2| CASNo_Comment = (anhydrous)

correct|CAS}}| CASNo2 = 6046-93-1| CASNo2_Comment = (hydrate)}}| Section2 = {{Chembox Properties| Formula = Cu(CH3COO)2| MolarMass = 181.63{{nbsp}}g/mol (anhydrous)199.65{{nbsp}}g/mol (hydrate)| Appearance = Dark green crystalline solid| Odor = Odorless (hydrate)

Hydrate: 7.2{{nbsp}}g/100{{nnbsp}}mL (cold water) 20{{nbsp}}g/100{{nnbsp}}mL (hot water)

ethanol>alcoholSlightly soluble in ether and glycerol| Density = 1.882{{nbsp}}g/cm3 (hydrate)| RefractIndex = 1.545 (hydrate) }}| Section3 = {{Chembox Structure| CrystalStruct = Monoclinic }}| Section4 = | Section5 = | Section6 = | Section7 = {{Chembox Hazards| ExternalSDS = Baker MSDS| NFPA-H = 2| NFPA-F = 0| NFPA-R = 0| FlashPt = Non-flammable| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}{{GHS09}}| GHSSignalWord = Danger

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ACCESSDATE=2011-06-14

ARCHIVE-URL=HTTPS://WEB.ARCHIVE.ORG/WEB/20110928193709/HTTP://WWW.SARGENTWELCH.COM/PDF/MSDS/COPPER_II_ACETATE_212.00.PDF, 2011-09-28,

0150}}| REL = TWA 1{{nbsp}}mg/m3 (as Cu)| IDLH = TWA 100{{nbsp}}mg/m3 (as Cu) }} }}Copper(II) acetate, also referred to as cupric acetate, is the chemical compound with the formula Cu(OAc)2 where AcO− is acetate ({{chem|CH|3|CO|2|−}}). The hydrated derivative, Cu2(OAc)4(H2O)2, which contains one molecule of water for each copper atom, is available commercially. Anhydrous copper(II) acetate is a dark green crystalline solid, whereas Cu2(OAc)4(H2O)2 is more bluish-green. Since ancient times, copper acetates of some form have been used as fungicides and green pigments. Today, copper acetates are used as reagents for the synthesis of various inorganic and organic compounds.{{Ullmann|first=H. Wayne|last=Richardson|title=Copper Compounds|DOI=10.1002/14356007.a07_567}} Copper acetate, like all copper compounds, emits a blue-green glow in a flame. Structure Copper acetate hydrate adopts the paddle wheel structure seen also for related Rh(II) and Cr(II) tetraacetates.JOURNAL, Van Niekerk, J. N., Schoening, F. R. L., X-Ray Evidence for Metal-to-Metal Bonds in Cupric and Chromous Acetate, Nature (journal), Nature, 1953, 171, 4340, 36–37, 10.1038/171036a0, 1953Natur.171...36V, 4292992, BOOK, Wells, A. F., 1984, Structural Inorganic Chemistry, Oxford, Clarendon Press, {{ISBN missing}} One oxygen atom on each acetate is bound to one copper atom at 1.97 Ã… (197 pm). Completing the coordination sphere are two water ligands, with Cu–O distances of 2.20 Ã… (220 pm). The two copper atoms are separated by only 2.62 Ã… (262 pm), which is close to the Cu–Cu separation in metallic copper.JOURNAL, J., Catterick, P., Thornton, Structures and physical properties of polynuclear carboxylates, Adv. Inorg. Chem. Radiochem., Advances in Inorganic Chemistry and Radiochemistry, 1977, 291–362, 20,weblink 10.1016/s0065-2792(08)60041-2, 9780120236206, JOURNAL, van Niekerk, J. N., Schoening, F. R. L., 1953-03-10, A new type of copper complex as found in the crystal structure of cupric acetate, Cu2(CH3COO)4.2H2O,weblink Acta Crystallographica, en, 6, 3, 227–232, 10.1107/S0365110X53000715, 0365-110X, free, 1953AcCry...6..227V, JOURNAL, Meester, Patrice de, Fletcher, Steven R., Skapski, Andrzej C., 1973-01-01, Refined crystal structure of tetra-µ-acetato-bisaquodicopper(II),weblink Journal of the Chemical Society, Dalton Transactions, en, 23, 2575–2578, 10.1039/DT9730002575, 1364-5447, JOURNAL, Brown, G. M., Chidambaram, R., 1973-11-15, Dinuclear copper(II) acetate monohydrate: a redetermination of the structure by neutron-diffraction analysis,weblink Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry, en, 29, 11, 2393–2403, 10.1107/S0567740873006758, 1973AcCrB..29.2393B, 0567-7408, The two copper centers interact resulting in a diminishing of the magnetic moment such that at temperatures below 90 K, Cu2(OAc)4(H2O)2 is essentially diamagnetic. Cu2(OAc)4(H2O)2 was a critical step in the development of modern theories for antiferromagnetic exchange coupling, which ascribe its low-temperature diamagnetic behavior to cancellation of the two opposing spins on the adjacent copper atoms.BOOK, Carlin, R. L., Magnetochemistry, 1986, Springer, 978-3642707353, Berlin, 77–82, {{Gallery |mode=packed |align=center

alt1=Copper(II) acetate monohydrate, dichroic|Copper(II) acetate monohydrate, dichroic}} Synthesis Copper(II) acetate is prepared industrially by heating copper(II) hydroxide or basic copper(II) carbonate with acetic acid. Uses in chemical synthesis Copper(II) acetate has found some use as an oxidizing agent in organic syntheses. In the Eglinton reaction Cu2(OAc)4 is used to couple terminal alkynes to give a 1,3-diyne:{{OrgSynth|first1=K.|last1=Stöckel|first2=F.|last2=Sondheimer|prep=CV6P0068|title=[18]Annulene|date=1974|volume=54|page=1|collvol=6|collvolpages=68|DOI=10.15227/orgsyn.054.0001}}{{OrgSynth|first1=I. D.|last1=Campbell|author2-link=Geoffrey Eglinton|first2=G.|last2=Eglinton|prep=CV5P0517|title=Diphenyldiacetylene|date=1965|volume=45|page=39|collvol=5|collvolpages=517|DOI=10.15227/orgsyn.045.0039}} Cu2(OAc)4 + 2 RC≡CH → 2 CuOAc + RC≡C−C≡CR + 2 HOAc The reaction proceeds via the intermediacy of copper(I) acetylides, which are then oxidized by the copper(II) acetate, releasing the acetylide radical. A related reaction involving copper acetylides is the synthesis of ynamines, terminal alkynes with amine groups using Cu2(OAc)4.ENCYCLOPEDIA, P., Vogel, J., Srogl, Copper(II) Acetate, EROS Encyclopedia of Reagents for Organic Synthesis, 2005, John Wiley & Sons, 10.1002/047084289X.rc194.pub2, 978-0-470-84289-8, . It has been used for hydroamination of acrylonitrile.{{OrgSynth|first=S. A.|last=Heininger|prep=CV4P0146|title=3-(o-Chloroanilino)propionitrile|date=1958|volume=38|page=14|collvol=4|collvolpages=146|DOI=10.15227/orgsyn.038.0014}}It is also an oxidising agent in Barfoed's test.It reacts with arsenic trioxide to form copper acetoarsenite, a powerful insecticide and fungicide called Paris green. Related compounds Heating a mixture of anhydrous copper(II) acetate and copper metal affords copper(I) acetate:BOOK, S. J., Kirchner, Q., Fernando, Inorganic Syntheses, Copper(I) Acetate, Inorg. Synth., 2007, 53–55, 10.1002/9780470132517.ch16, 20, 9780470132517, ENCYCLOPEDIA, Parish, E. J., Kizito, S. A., Copper(I) Acetate, Encyclopedia of Reagents for Organic Synthesis, 2001, John Wiley & Sons, 10.1002/047084289X.rc193, 0471936235, Cu + Cu(OAc)2 → 2 CuOAc Unlike the copper(II) derivative, copper(I) acetate is colourless and diamagnetic."Basic copper acetate" is prepared by neutralizing an aqueous solution of copper(II) acetate. The basic acetate is poorly soluble. This material is a component of verdigris, the blue-green substance that forms on copper during long exposures to atmosphere. Other Uses A mixture of copper acetate and ammonium chloride is used to chemically color copper with a bronze patina.WEB, Budija, Goran, Collection of formulas for the chemical,electrochemical and heat colouring of metals,the cyanide free immersion plating and electroplating,weblink Finishing.com, December 30, 2023, Mineralogy The mineral hoganite is a naturally occurring form of copper(II) acetate.JOURNAL, 2007-05-01, A spectroscopic and thermoanalytical study of the mineral hoganite,weblink Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, en, 67, 1, 48–57, 10.1016/j.saa.2006.05.037, 1386-1425, Musumeci, Anthony, Frost, Ray L., 17321784, 2007AcSpA..67...48M, JOURNAL, Hibbs, D. E., Kolitsch, U., Leverett, P., Sharpe, J. L., Williams, P. A., June 2002, Hoganite and paceite, two new acetate minerals from the Potosi mine, Broken Hill, Australia,weblink Mineralogical Magazine, en, 66, 3, 459–464, 10.1180/0026461026630042, 2002MinM...66..459H, 97116531, 0026-461X, A related mineral, also containing calcium, is paceite. Both are very rare.WEB,weblink Paceite, WEB,weblink List of Minerals, 21 March 2011, {{Gallery |mode=packed |align=center

alt2=Copper acetate, crystalline|Copper(II) acetate, crystalline

alt3=Copper acetate, milled|Copper(II) acetate, milled}}{{clear}} References {{Reflist}} External links {{Commons category|Copper(II) acetate}} Copper.org – Other Copper Compounds {{Webarchive|url=https://web.archive.org/web/20130815084358weblink |date=2013-08-15 }} 5 Feb. 2006 Infoplease.com – Paris green 6 Feb. 2006 Verdigris – History and Synthesis 6 Feb. 2006 Australian - National Pollutant Inventory 8 Aug. 2016 USA NIH National Center for Biotechnology Information 8 Aug. 2016 {{Copper compounds}}{{Acetates}}