Copper(II) acetate

Small crystals of copper(II) acetate

Copper(II) acetate monohydrate

Names
IUPAC name

Tetra-μ2-acetatodiaquadicopper(II)

Other names

Copper(II) ethanoate
Cupric acetate
Copper acetate
Verdigris

Identifiers

CAS Number

* 142-71-2 (anhydrous) Y
* 6046-93-1 (hydrate) Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 8555 Y

EC Number |

* 205-553-3

PubChem CID

* 8895

UNII |

* 39M11XPH03 (anhydrous) Y
* 39J9V52S86 (hydrate) Y

UN number | 3077

InChI

* InChI=1S/2C2H4O2.Cu/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2 Y

Key: OPQARKPSCNTWTJ-UHFFFAOYSA-L Y

* InChI=1/2C2H4O2.Cu/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2

Key: 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

Properties

Chemical formula

| Cu(CH3COO)2
Molar mass | 181.63 g/mol (anhydrous)
199.65 g/mol (hydrate)
Appearance  | Dark green crystalline solid
Odor | Odorless (hydrate)
Density | 1.882 g/cm3 (hydrate)
Melting point | 115 °C (anhydrous) [1]

Undetermined (hydrate)[2]

Boiling point |  240 °C (464 °F; 513 K)

Solubility in water

| Hydrate:
7.2 g/100 mL (cold water)
20 g/100 mL (hot water)
Solubility | Soluble in alcohol
Slightly soluble in ether and glycerol

Refractive index (nD)

| 1.545 (hydrate)
Structure

Crystal structure

| Monoclinic
Hazards
Safety data sheet | Baker MSDS
GHS pictograms |
GHS Signal word | Danger

GHS hazard statements

| H301, H302, H311, H314, H410, H411, H412

GHS precautionary statements

| P260, P264, P270, P273, P280, P301+310, P301+312, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P312, P321, P322, P330, P361, P363, P391, P405, P501
NFPA 704 (fire diamond)  |

Flash point | Non-flammable
Lethal dose or concentration (LD, LC):

LD50 (median dose)

| 710 mg/kg oral rat[4]
NIOSH (US health exposure limits):

PEL (Permissible)

| TWA 1 mg/m3 (as Cu)[3]

REL (Recommended)

| TWA 1 mg/m3 (as Cu)[3]

IDLH (Immediate danger)

| TWA 100 mg/m3 (as Cu)[3]

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Copper(II) acetate, also referred to as cupric acetate, is the chemical compound with the formula Cu(OAc)2 where AcO− is acetate (CH3CO−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.[5] Copper acetate, like all copper compounds, emits a blue-green glow in a flame.

## Contents

* 1 Structure
* 2 Synthesis
* 3 Uses in chemical synthesis
* 3.1 Related compounds
* 4 Other Uses
* 5 Mineralogy
* 6 References
* 7 External links

## Structure

Copper acetate hydrate adopts the paddle wheel structure seen also for related Rh(II) and Cr(II) tetraacetates.[6][7] One oxygen atom on each acetate is bound to one copper atom at 1.97 Å (197 pm). Completing the coordination sphere are two water ligands, with Cu–O distances of 2.20 Å (220 pm). The two copper atoms are separated by only 2.62 Å (262 pm), which is close to the Cu–Cu separation in metallic copper.[8][9][10][11] 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.[12]

* 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.[5]

## 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:[13][14]

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.[15] It has been used for hydroamination of acrylonitrile.[16]

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:[17][18]

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.[19]

## Mineralogy

The mineral hoganite is a naturally occurring form of copper(II) acetate.[20][21] A related mineral, also containing calcium, is paceite.[21] Both are very rare.[22][23]

* Copper(II) acetate, crystalline

* Copper(II) acetate, milled

## References

1. ↑ https://www.chemspider.com/Chemical-Structure.8555.html
2. ↑ Trimble, R. F. (1976). "Copper(II) acetate monohydrate - An erroneous melting point". Journal of Chemical Education 53 (6): 397. doi:10.1021/ed053p397. Bibcode: 1976JChEd..53..397T.
3. ↑ 3.0 3.1 3.2 NIOSH Pocket Guide to Chemical Hazards. "#0150". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0150.html.
4. ↑ "Mineral Safety Data Sheet: Copper (II) Acetate, Monohydrate". Archived on 2011-09-28. Error: If you specify `|archivedate=`, you must also specify `|archiveurl=`. http://www.sargentwelch.com/pdf/msds/Copper_II_Acetate_212.00.pdf. Retrieved 2011-06-14.
5. ↑ 5.0 5.1 Richardson, H. Wayne. "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH.
6. ↑ Van Niekerk, J. N.; Schoening, F. R. L. (1953). "X-Ray Evidence for Metal-to-Metal Bonds in Cupric and Chromous Acetate". Nature 171 (4340): 36–37. doi:10.1038/171036a0. Bibcode: 1953Natur.171...36V.
7. ↑ Wells, A. F. (1984). Structural Inorganic Chemistry. Oxford: Clarendon Press. [ISBN missing]
8. ↑ Catterick, J.; Thornton, P. (1977). "Structures and physical properties of polynuclear carboxylates". Adv. Inorg. Chem. Radiochem.. Advances in Inorganic Chemistry and Radiochemistry 20: 291–362. doi:10.1016/s0065-2792(08)60041-2. ISBN 9780120236206. https://books.google.com/books?id=es-Pu2hI5swC&q=related:VV11sw7b1OoJ:scholar.google.com/&pg=PA291.
9. ↑ 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" (in en). Acta Crystallographica 6 (3): 227–232. doi:10.1107/S0365110X53000715. ISSN 0365-110X. https://scripts.iucr.org/cgi-bin/paper?a00857.
10. ↑ Meester, Patrice de; Fletcher, Steven R.; Skapski, Andrzej C. (1973-01-01). "Refined crystal structure of tetra-µ-acetato-bisaquodicopper(II)" (in en). Journal of the Chemical Society, Dalton Transactions (23): 2575–2578. doi:10.1039/DT9730002575. ISSN 1364-5447. https://pubs.rsc.org/en/content/articlelanding/1973/dt/dt9730002575.
11. ↑ Brown, G. M.; Chidambaram, R. (1973-11-15). "Dinuclear copper(II) acetate monohydrate: a redetermination of the structure by neutron-diffraction analysis" (in en). Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry 29 (11): 2393–2403. doi:10.1107/S0567740873006758. ISSN 0567-7408. http://scripts.iucr.org/cgi-bin/paper?S0567740873006758.
12. ↑ Carlin, R. L. (1986). Magnetochemistry. Berlin: Springer. pp. 77–82. ISBN 978-3642707353.
13. ↑ Stöckel, K.; Sondheimer, F.. "[18Annulene"]. Organic Syntheses 54: 1. doi:10.15227/orgsyn.054.0001. http://www.orgsyn.org/demo.aspx?prep=CV6P0068. ;  Collective Volume, 6, pp. 68
14. ↑ Campbell, I. D.; Eglinton, G.. "Diphenyldiacetylene". Organic Syntheses 45: 39. doi:10.15227/orgsyn.045.0039. http://www.orgsyn.org/demo.aspx?prep=CV5P0517. ;  Collective Volume, 5, pp. 517
15. ↑ Vogel, P.; Srogl, J. (2005). "Copper(II) Acetate". EROS Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rc194.pub2. ISBN 978-0-470-84289-8. .
16. ↑ Heininger, S. A.. "3-(o-Chloroanilino)propionitrile". Organic Syntheses 38: 14. doi:10.15227/orgsyn.038.0014. http://www.orgsyn.org/demo.aspx?prep=CV4P0146. ;  Collective Volume, 4, pp. 146
17. ↑ Kirchner, S. J.; Fernando, Q. (2007). "Copper(I) Acetate". Inorganic Syntheses. 20. 53–55. doi:10.1002/9780470132517.ch16. ISBN 9780470132517.
18. ↑ Parish, E. J.; Kizito, S. A. (2001). "Copper(I) Acetate". Encyclopedia of Reagents for Organic Synthesis. John Wiley & Sons. doi:10.1002/047084289X.rc193. ISBN 0471936235.
19. ↑ Budija, Goran. "Collection of formulas for the chemical,electrochemical and heat colouring of metals,the cyanide free immersion plating and electroplating". https://www.finishing.com/library/budija/budija.pdf.
20. ↑ Musumeci, Anthony; Frost, Ray L. (2007-05-01). "A spectroscopic and thermoanalytical study of the mineral hoganite" (in en). Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 67 (1): 48–57. doi:10.1016/j.saa.2006.05.037. ISSN 1386-1425. PMID 17321784. Bibcode: 2007AcSpA..67...48M. https://www.sciencedirect.com/science/article/abs/pii/S1386142506003787.
21. ↑ 21.0 21.1 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" (in en). Mineralogical Magazine 66 (3): 459–464. doi:10.1180/0026461026630042. ISSN 0026-461X. Bibcode: 2002MinM...66..459H. https://www.cambridge.org/core/product/identifier/S0026461X00045783/type/journal_article.
22. ↑ "Paceite". https://www.mindat.org/min-10918.html.
23. ↑ "List of Minerals". 21 March 2011. https://www.ima-mineralogy.org/Minlist.htm.

## External links

* Copper.org – Other Copper Compounds 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

* v
* t
* e

Copper compounds

Cu(0,I)|

* Cu5Si

Cu(I)|

* CuBr
* CuCN
* CuCl
* CuF
* CuH
* CuI
* Cu2C2
* Cu2Cr2O5
* Cu2O
* CuOH
* CuNO3
* Cu3P
* Cu2S
* CuSCN

Cu(I,II)|

* Cu3H4O8S2

Cu(II)|

* Cu(BF4)2
* CuBr2
* CuC2
* CuCO3
* Cu(CN)2
* Cu(ClO3)2
* CuCl2
* CuF2
* Cu(NO3)2
* Cu3(PO4)2
* Cu(N3)2
* CuO
* CuO2
* Cu(OH)2
* CuI2
* CuS
* CuSO4
* Cu3(AsO4)2

Cu(III)|

* K3CuF6
* Cu2O3

Cu(IV)|

* Cs2CuF6
* Rb2CuF6

* v
* t
* e

Acetyl halides and salts of the acetate ion

AcOH |  |  |  | He
LiOAc | Be(OAc)2
BeAcOH | B(OAc)3 | AcOAc
ROAc | NH4OAc | AcOOH | FAc | Ne
NaOAc | Mg(OAc)2 | Al(OAc)3
ALSOL
Al(OAc)2OH
Al2SO4(OAc)4 | Si  | P  | S  | ClAc | Ar
KOAc | Ca(OAc)2 | Sc(OAc)3 | Ti(OAc)4 | VO(OAc)3 | Cr(OAc)2
Cr(OAc)3 | Mn(OAc)2
Mn(OAc)3 | Fe(OAc)2
Fe(OAc)3 | Co(OAc)2,
Co(OAc)3 | Ni(OAc)2 | Cu(OAc)2 | Zn(OAc)2 | Ga(OAc)3 | Ge  | As(OAc)3 | Se  | BrAc | Kr
RbOAc | Sr(OAc)2 | Y(OAc)3 | Zr(OAc)4 | Nb  | Mo(OAc)2 | Tc  | Ru(OAc)2
Ru(OAc)3
Ru(OAc)4 | Rh2(OAc)4 | Pd(OAc)2 | AgOAc | Cd(OAc)2 | In  | Sn(OAc)2
Sn(OAc)4 | Sb(OAc)3 | Te  | IAc | Xe
CsOAc | Ba(OAc)2 |  | Hf  | Ta  | W  | Re  | Os  | Ir  | Pt(OAc)2 | Au  | Hg2(OAc)2,
Hg(OAc)2 | TlOAc
Tl(OAc)3 | Pb(OAc)2
Pb(OAc)4 | Bi(OAc)3 | Po  | At  | Rn
Fr  | Ra  |  | Rf  | Db  | Sg  | Bh  | Hs  | Mt  | Ds  | Rg  | Cn  | Nh  | Fl  | Mc  | Lv  | Ts  | Og
| ↓  |  |
La(OAc)3 | Ce(OAc)x | Pr  | Nd  | Pm  | Sm(OAc)3 | Eu(OAc)3 | Gd(OAc)3 | Tb  | Dy(OAc)3 | Ho(OAc)3 | Er  | Tm  | Yb(OAc)3 | Lu(OAc)3
Ac  | Th  | Pa  | UO2(OAc)2 | Np  | Pu  | Am  | Cm  | Bk  | Cf  | Es  | Fm  | Md  | No  | Lr

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*[CID]: Compound ID
*[H301]: Toxic if swallowed
*[H302]: Harmful if swallowed
*[H311]: Toxic in contact with skin
*[H314]: Causes severe skin burns and eye damage
*[H410]: Very toxic to aquatic life with long lasting effects
*[H411]: Toxic to aquatic life with long lasting effects
*[H412]: Harmful to aquatic life with long lasting effects
*[P260]: Do not breathe dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P270]: Do not eat, drink or smoke when using this product
*[P273]: Avoid release to the environment
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P301+310]: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician
*[P301+312]: IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell
*[P301+330+331]: IF SWALLOWED: Rinse mouth. Do NOT induce vomiting
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P310]: Immediately call a POISON CENTER or doctor/physician
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P322]: Specific measures (see … on this label)
*[P330]: Rinse mouth
*[P361]: Remove/Take off immediately all contaminated clothing
*[P363]: Wash contaminated clothing before reuse
*[P391]: Collect spillage
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …
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