Copper(II) acetate

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
Copper(II) acetate
hydrated derivative, which contains one molecule of water for each Cu atom, is available commercially. Anhydrous Cu(OAc)2 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.[4] Copper acetate, like all copper
compounds, emits a blue-green glow in aflame. The mineral hoganite is a naturally occurring form of copper(II) acetate.

Contents
Structure
Small crystals of copper(II) acetate
Synthesis
Related compounds
Uses in chemical synthesis
References
External links

Structure
Copper acetate hydrate adopts the paddle wheel structure seen also for related Rh(II) and Cr(II)
tetraacetates.[5][6] One oxygen atom on each acetate is bound to one copper 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 five-
coordinate copper atoms are separated by only 2.62 Å (262 pm), which is close to the Cu–Cu separation in
metallic copper.[7] The two copper centers interact resulting in a diminishing of the magnetic moment such
Copper(II) acetate crystals on copper
that near 90 K, Cu2(OAc)4(H2O)2 is essentially diamagnetic due to cancellation of the two opposing spins.
wire
Cu2(OAc)4(H2O)2 was a critical step in the development of modern theories for antiferromagnetic
coupling.[8] Names
IUPAC name
The dinuclear structure of dimeric
Tetra-μ2-
copper(II) acetate hydrate Synthesis
acetatodiaquadicopper(II)
Copper(II) acetate is prepared industrially by heating copper(II) hydroxide or copper(II) carbonate with
Other names
acetic acid.[4]
Copper(II) ethanoate
Cupric acetate
Related compounds Copper Acetate
Verdigris
fords copper(I) acetate:[9][10]
Heating a mixture of anhydrous copper(II) acetate and copper metal af
Identifiers
Cu + Cu(OAc)2 → 2 CuOAc CAS Number 142-71-2
(anhydrous)
Unlike the copper(II) derivative, copper(I) acetate is colourless and diamagnetic.
6046-93-1
"Basic copper acetate" is prepared by neutralizing an aqueous solution of copper(II) acetate. The basic acetate is poorly soluble. This material is a (hydrate) ‹See TfM›
component of verdigris, the blue-green substance that forms on copper during long exposures to atmosphere.

3D model (JSmol) Interactive

Uses in chemical synthesis image
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 ChemSpider 8555
to give a 1,3-diyne:[11][12]
ECHA InfoCard 100.005.049
Cu2(OAc)4 + 2 RC≡CH → 2 CuOAc + RC≡C−C≡CR + 2 HOAc PubChem CID 8895

The reaction proceeds via the intermediacy of copper(I) acetylides, which are then oxidized by the copper(II) acetate, releasing the acetylide radical. A UNII 39M11XPH03
related reaction involving copper acetylides is the synthesis of ynamines, terminal alkynes with amine groups using Cu2(OAc)4.[13] It has been used for InChI
hydroamination of acrylonitrile.[14]
SMILES
It is also an oxidising agent inBarfoed's test. Properties
Chemical formula Cu(CH3COO)2
It combines with arsenic trioxide to form copper acetoarsenite, a powerfulinsecticide and fungicide called Paris Green or Schweinfurt Green.
Molar mass 181.63 g/mol
(anhydrous)
References 199.65 g/mol
(hydrate)
1. Trimble, R. F. "Copper(II) acetate monohydrate - An erroneous melting point".Journal of Chemical Education. 53: 397.
doi:10.1021/ed053p397 (https://doi.org/10.1021%2Fed053p397). Appearance Dark green
2. "NIOSH Pocket Guide to Chemical Hazards #0150"(https://www.cdc.gov/niosh/npg/npgd0150.html). National Institute for Occupational crystalline solid
Safety and Health (NIOSH). Odor odorless
3. "Archived copy" (https://web.archive.org/web/20110928193709/http://www .sargentwelch.com/pdf/msds/Copper_II_Acetate_212.00.pdf) (hydrate)
(PDF). Archived from the original (http://www.sargentwelch.com/pdf/msds/Copper_II_Acetate_212.00.pdf)(PDF) on 2011-09-28.
Retrieved 2011-06-14. Density 1.882 g/cm3
4. Richardson, H. Wayne, "Copper Compounds", Ullmann's Encyclopedia of Industrial Chemistry
, Weinheim: Wiley-VCH (hydrate)
5. Van Niekerk, J. N.; Schoening, F. R. L. (1953). "X-Ray Evidence for Metal-to-Metal Bondsin Cupric and Chromous Acetate".Nature. Melting point Undetermined
171 (4340): 36–37. doi:10.1038/171036a0 (https://doi.org/10.1038%2F171036a0). [1]

6. Wells, A. F. (1984). Structural Inorganic Chemistry. Oxford: Clarendon Press. Boiling point 240 °C (464 °F;
 7. Catterick, J.; Thornton, P. (1977). "Structures and physical properties of polynuclear carboxylates"(https://books.google.com/books?hl 513 K)
=ru&lr=&id=es-Pu2hI5swC&oi=fnd&pg=P A291&dq=related:VV11sw7b1OoJ:scholar.google.com/&ots=o59nIGR4M_&sig=eGl5rS_sRb8
Solubility in water hydrate:
5QsezUdvD8O3WB8I#v=onepage&q&f=false) . Adv. Inorg. Chem. Radiochem. 20: 291–362. doi:10.1016/s0065-2792(08)60041-2(http
s://doi.org/10.1016%2Fs0065-2792%2808%2960041-2) .
7.2 g/100 mL
(cold water)
8. Carlin, R. L. (1986). Magnetochemistry. Berlin: Springer.
20 g/100 mL
9. Kirchner, S. J.; Fernando, Q. (1980). "Copper(I) Acetate". Inorg. Synth. 20: 53–55. doi:10.1002/9780470132517.ch16(https://doi.org/1
0.1002%2F9780470132517.ch16). (hot water)
10. Parish, E. J.; Kizito, S. A. (2001). "Copper(I) Acetate".Encyclopedia of Reagents for Organic Synthesis
. John Wiley & Sons. Solubility Soluble in
doi:10.1002/047084289X.rc193(https://doi.org/10.1002%2F047084289X.rc193) . alcohol
11. Stöckel, K.; Sondheimer, F. "[18]Annulene" (http://www.orgsyn.org/demo.aspx?prep=CV6P0068). Organic Syntheses. 54: 1. Slightly soluble
doi:10.15227/orgsyn.054.0001(https://doi.org/10.15227%2Forgsyn.054.0001) .; Collective Volume, 6, p. 68 in ether and
12. Campbell, I. D.; Eglinton, G. "Diphenyldiacetylene" (http://www.orgsyn.org/demo.aspx?prep=CV5P0517). Organic Syntheses. 45: 39. glycerol
doi:10.15227/orgsyn.045.0039(https://doi.org/10.15227%2Forgsyn.045.0039) .; Collective Volume, 5, p. 517
Refractive index 1.545 (hydrate)
13. Vogel, P.; Srogl, J. (2005). "Copper(II) Acetate". EROS Encyclopedia of Reagents for Organic Synthesis
. John Wiley & Sons. (nD)
doi:10.1002/047084289X.rc194.pub2(https://doi.org/10.1002%2F047084289X.rc194.pub2) . ISBN 978-0-470-84289-8..
Structure
14. Heininger, S. A. "3-(o-Chloroanilino)propionitrile"(http://www.orgsyn.org/demo.aspx?prep=CV4P0146). Organic Syntheses. 38: 14.
doi:10.15227/orgsyn.038.0014(https://doi.org/10.15227%2Forgsyn.038.0014) .; Collective Volume, 4, p. 146 Crystal structure Monoclinic
Hazards
Safety data sheet Baker MSDS
External links
R-phrases 22-36/37/38-
Copper.org – Other Copper Compounds5 Feb. 2006 (outdated) 50/53
Infoplease.com – Paris green6 Feb. 2006
S-phrases 26-60-61
Verdigris – History and Synthesis6 Feb. 2006
(outdated)
Australian - National Pollutant Inventory8 Aug. 2016
USA NIH National Center for Biotechnology Information8 Aug. 2016 NFPA 704
0
2 0

Flash point Non-flammable

Lethal dose or concentration (LD,
LC):
LD50 (median 710mg/kg oral
dose) rat [3]
US health exposure limits (NIOSH):
PEL TWA 1 mg/m3
(Permissible) (as Cu)[2]
REL TWA 1 mg/m3
(Recommended) (as Cu)[2]

IDLH TWA 100 mg/m3

(Immediate (as Cu)[2]
danger)
Except where otherwise noted, data
are given for materials in their
standard state (at 25 °C [77 °F],
100 kPa).
‹See TfM›
‹See TfM› verify (what is ?)

Infobox references

Acetyl halides and salts of the acetate ion

AcOH
Be(OAc)2 AcOAc
LiOAc B(OAc)3 NH
BeAcOH ROAc
Al(OAc)3
ALSOL
NaOAc Mg(OAc)2 Al(OAc)2OH Si P
Al2SO4(OAc)4
Cr(OAc)2 Mn(OAc)2 Fe(OAc)2 Co(OAc)2,
KOAc Ca(OAc)2 Sc(OAc)3 Ti(OAc)4 VO(OAc)3 Ni(OAc)2 Cu(OAc)2 Zn(OAc)2 Ga(OAc)3 Ge As(OAc)
Cr(OAc) 3 Mn(OAc)3 Fe(OAc)3 Co(OAc)3
Ru(OAc)2
Sn(OAc)2
RbOAc Sr(OAc)2 Y(OAc)3 Zr(OAc)4 Nb Mo(OAc)2 Tc Ru(OAc)3 Rh2(OAc)4 Pd(OAc)2 AgOAc Cd(OAc)2 In Sb(OAc)
Sn(OAc)4
Ru(OAc)4
Hg2(OAc)2, TlOAc Pb(OAc)2
CsOAc Ba(OAc)2 Hf Ta W Re Os Ir Pt(OAc)2 Au Bi(OAc)
Hg(OAc)2 Tl(OAc)3 Pb(OAc)4
Fr Ra Rf Db Sg Bh Hs Mt Ds Rg Cn Nh Fl Mc
↓
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
Ac Th Pa UO2(OAc)2 Np Pu Am Cm Bk Cf Es Fm Md

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