142-71-2 Usage
Physical Properties
Bluish-green fine powder; hygroscopic. The monohydrate is dimeric; density 1.88 g/cm3; melts at 115°C; decomposes at 240°C; soluble in water and ethanol; and slightly soluble in ether.
Uses
Different sources of media describe the Uses of 142-71-2 differently. You can refer to the following data:
1. Copper(II) acetate is used as a pigment for ceramics; in the manufacture of Paris green; in textile dyeing; as a fungicide; and as a catalyst.
2. Used as a catalyst or oxidizing agent in organic syntheses
3. Used in biochemical applications such as DNA extraction
4. Copper(II) acetate is used in biochemical applications such as DNA extraction. It is used as a source of copper in inorganic synthesis, an oxidizing agent and catalyst in organic synthesis. It is also used to couple two terminal alkynes to make a 1,3-diyne. It is widely used in pigments, manufacture of paris green, textile dyeing, skin conditioner in cosmetics, antioxidant and stabilizer in food grade polymers.
Preparation
Copper(II) acetate is prepared by treatment of copper(II) oxide, CuO, or copper(II) carbonate, CuCO3, with acetic acid, followed by crystallization: CuO + 2CH3COOH → (CH3COO)2Cu + H2O
Toxicity
Copper(II) acetate is moderately toxic by ingestion and possibly other routes of administration. LD50 oral (rat): c. 600 mg/kg
Description
Copper (II) acetate, also referred to as cupric acetate, is the chemical compound with the formula Cu(OAc)22 where OAc- is acetate (CH3CO2-). The 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. Copper acetate, like all copper compounds, emits a blue-green glow in a flame.
Chemical Properties
Cupric acetate is a greenish Blue powder or small crystals.
History
Copper (II) acetate was historically prepared in vineyards, since acetic acid is a byproduct of fermentation. Copper sheets were alternately layered with fermented grape skins and dregs left over from wine production and exposed to air. This would leave a blue substance on the outside of the sheet. This was then scraped off and dissolved in water. The resulting solid was used as a pigment, or combined with arsenic trioxide to form copper acetoarsenite, a powerful insecticide and fungicide called Paris Green or Schweinfurt Green. During the Second World War copper acetate was used as shark repellent . Under war conditions, before adoption it has been tested only very briefly (while in general successfully). The source says copper acetate does repel sharks in some situations but not in all.
Application
The uses for copper (II) acetate are more plentiful as a catalyst or oxidizing agent in organic syntheses. For example, Cu2(OAc)4 is used to couple two terminal alkynes to make a 1,3-diyne: 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.
General Description
A blue-green crystalline solid. The primary hazard is the threat to the environment. Immediate steps should be taken to limit its spread to the environment. Cupric acetate is used as an insecticide, in the preparation of other chemicals, as a fungicide, and mildew preventive.
Air & Water Reactions
Water soluble.
Reactivity Profile
Salts, basic, such as Cupric acetate, are generally soluble in water. The resulting solutions contain moderate concentrations of hydroxide ions and have pH's greater than 7.0. They react as bases to neutralize acids. These neutralizations generate heat, but less or far less than is generated by neutralization of the bases in reactivity group 10 (Bases) and the neutralization of amines. They usually do not react as either oxidizing agents or reducing agents but such behavior is not impossible.
Health Hazard
Inhalation of dust causes irritation of throat and lungs. Ingestion of large amounts causes violent vomiting and purging, intense pain, collapse, coma, convulsions, and paralysis. Contact with solutions irritates eyes; contact with solid causes severe eye surface injury and irritation of skin.
Fire Hazard
Special Hazards of Combustion Products: Irritating vapors of acetic acid may form in fires.
Safety Profile
Poison by
subcutaneous and intraperitoneal routes.
Moderately toxic by ingestion.
Experimental reproductive effects. When
heated to decomposition it emits acrid
smoke and irritating fumes. See also
COPPER COMPOUNDS.
Synthesis
Copper (II) acetate synthesized by the method described in the history section leads to impure samples. It is prepared industrially by heating copper (II) hydroxide or copper (II) carbonate with acetic acid. A second method of copper acetate production is to electrolyze a concentrated aqueous solution of calcium acetate with copper electrodes. As the reaction proceeds the anode oxidizes to produce copper acetate which adheres to its surface and can be removed as crystals. At the cathode calcium ions are reduced to calcium atoms and would be deposited, but due to the water content of the solution the calcium is converted to insoluble calcium hydroxide. The drawback with this setup is that the cathode gets coated with an insulating layer of calcium hydroxide, which gradually slows the process. To negate this hydroxide buildup mercury is utilized as the cathode; therefore as the process takes place the calcium formed immediately reacts with the mercury to make a calcium-mercury amalgam and the copper acetate formed at the anode is removed periodically. This process generally yields suitably pure copper acetate, on a small scale, with slight traces of calcium acetate. Copper (II) acetate also forms by treating copper metal with a solution of acetic acid and hydrogen peroxide.
Potential Exposure
Cupric acetate is used as a fungicide, as a catalyst for organic reactions; in textile dyeing and as a pigment for ceramics.
Shipping
UN3077 Environmentally hazardous substances, solid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material, Technical Name Required.
Purification Methods
Recystallise it twice from warm dilute acetic acid solutions (5mL/g) by cooling. [Beilstein 2 IV 111.]
Incompatibilities
Forms explosive materials with acetylene gas, ammonia, caustic solutions; sodium hypobromite; notromethane. Keep away from chemically active metals; strong acids; nitrates. Decomposes above 240C forming acetic acid fumes
Waste Disposal
Copper-containing soluble wastes can be concentrated through the use of ion exchange, reverse osmosis, or evaporators to the point where copper can be electrolytically removed and sent to a reclaiming firm. If recovery is not feasible, the copper can be precipitated through the use of caustics and the sludge deposited in a chemical waste landfill.
Check Digit Verification of cas no
The CAS Registry Mumber 142-71-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 2 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 142-71:
(5*1)+(4*4)+(3*2)+(2*7)+(1*1)=42
42 % 10 = 2
So 142-71-2 is a valid CAS Registry Number.
InChI:InChI=1/2C2H4O2.Cu/c2*1-2(3)4;/h2*1H3,(H,3,4);/q;;+2/p-2/rC4H6CuO4/c1-3(6)8-5-9-4(2)7/h1-2H3
142-71-2Relevant articles and documents
Edwards,Richards
, p. 407,408, 411 (1975)
Weller,Mills
, p. 769,770 (1953)
A combined experimental and computational investigation on Tetrakis-μ-acetato-bis(acetamido)dicopper(II) and its application as a single source precursor for copper oxide
Trivedi, Manoj,Nagarajan,Kumar, Abhinav,Molloy, Kieran C.,Kociok-K?hn, Gabriele,Sudlow, Anna L.
, p. 920 - 924 (2011)
The physico-chemical properties of the Tetrakis-μ-acetato-bis(acetamido) dicopper(II) [Cu(O2CCH3)2(CH 3CONH2)]2 (1), have been thoroughly investigated via an integrated multi-technique experimental-computational approach. In the newly found orthorhombic compound, as revealed by low temperature single-crystal X-ray studies, the complex is present as centrosymmetrical dimeric unit, has a paddle-wheel conformation with four acetate ligands bridging two symmetry-related CuII ions. The distorted octahedral coordination environment around the CuII ion is completed by an oxygen atom from an acetamide ligand. The compound sublimates, without premature side decompositions, at 180 °C. The structural, electronic and thermal behavior of the neutral complex (1) has been investigated. The present study suggests application of [Cu(O2CCH3) 2(CH3CONH2)]2 (1) as a precursor for copper-based materials by Chemical Vapor Deposition.
Protolytic dissociation mechanisms and comparative acid stabilities of palladium(II), zinc(II), copper(II), and nickel(II) complexes of alkylated dipyrrins
Rumyantsev, Evgeniy V.,Marfin, Yuriy S.
, p. 699 - 704 (2014)
Complexes of Pd(II), Cu(II), Ni(II), and Zn(II) with alkylated dipyrrins (Hdpm) were synthesized and characterized by physicochemical and spectroscopic methods. Protolytic dissociation kinetics of these complexes in benzene in the presence of acetic and trichloroacetic acid was studied. A protonated dipyrrin is the reaction product of protolytic dissociation of the complexes in acid solutions. The observed and true dissociation rate constants, as well as activation reaction parameters, were calculated. Kinetic models of the processes are proposed, and the patterns of influence of the ligand nature on dissociation kinetics were determined. The Pd(II) complexes proved to be much more stable than other those of the other metals, according to the results of the kinetic studies. The lability of the complexes strongly depends on the length and position of the alkyl substituent of the ligand. The dissociation of the Ni(II) complex gives a heteroligand complex at low concentrations of acid, but the complex undergoes full protolytic dissociation at higher concentrations of acid. The dissociation of the complex of Cu(II) is an equilibrium process, involving formation of the protonated form of the ligand.
Teica, Diana T.,Segal, E.,Andruh, Marius
, p. 249 - 256 (1991)
The kinetics of complex formation in the trithiadiazoletri[3,4-di(4-tert- butylphenyl)-pyrrole] macrocycle-copper(ii) acetate-dmfa-h2o system
Lomova,Mozhzhukhina,Danilova,Islyaikin
, p. 1694 - 1700 (2009)
The paper presents the results of a study of the kinetics of coordination of a macroheterocyclic compound with an increased coordination cavity of the (3 + 3) McH3 composition consisting of sequentially alternating 1,3,4-thiadiazole and 3,4-bis
Cobalt, nickel, copper and cadmium coordination polymers containing the bis(1,2,4-triazolyl)methane ligand
Marchetti, Fabio,Masciocchi, Norberto,Albisetti, Alessandro Figini,Pettinari, Claudio,Pettinari, Riccardo
, p. 32 - 39 (2011)
Co(II), Ni(II), Cu(II) and Cd(II) coordination polymers containing the flexible ditopic bis(1,2,4-triazol-1-yl)methane ligand (Btm) have been prepared by reaction of equimolar quantities of the corresponding cobalt, nickel, copper and cadmium salts in EtOH solution. Structure solution and refinement of polycrystalline materials were performed by powder diffraction technique (XRPD), using conventional laboratory data. The results show that architecturally different coordination polymers were obtained depending on the counter-ion employed. The XRPD results show also that non-covalent interactions are driving forces for the occurrence of different structures.
Kinetic stability of complexes of some d-metals with 3,3'- bis(dipyrrolylmethene) in the binary proton-donor solvent acetic acid-benzene
Antina,Guseva,V'yugin,Antina
, (2012)
The kinetics of dissociation of Co(II), Ni(II), Cu(II), Zn(II), Cd(II), and Hg(II) binuclear homoleptic double-stranded helicates with bis(2,4,7,8,9- pentametyldipyrrolylmethen-3-yl)methane (H2L) of the [M 2L2] composition
OPTICAL FILTER AND IMAGING APPARATUS
-
, (2020/12/29)
An optical filter (1a) includes a light-absorbing layer (10). The light-absorbing layer absorbs light in at least a portion of the near-infrared region. When light with a wavelength of 300 to 1200 nm is incident on the optical filter (1a) at an incident angle of 0°, the optical filter (1a) satisfies given requirements. When light with a wavelength of 300 to 1200 nm is incident on the optical filter (1a) at incident angles of 0°, 30°, 35°, and 40°, the optical filter (1a) satisfies given requirements related to a normalized spectral transmittance. The normalized spectral transmittance is determined by normalization of a spectral transmittance for each incident angle so that the maximum of the spectral transmittance for each incident angle in the wavelength range of 400 to 650 nm is 100%.
Efficient Copper-Catalyzed Multicomponent Synthesis of N-Acyl Amidines via Acyl Nitrenes
Van Vliet, Kaj M.,Polak, Lara H.,Siegler, Maxime A.,Van Der Vlugt, Jarl Ivar,Guerra, Célia Fonseca,De Bruin, Bas
supporting information, p. 15240 - 15249 (2019/10/19)
Direct synthetic routes to amidines are desired, as they are widely present in many biologically active compounds and organometallic complexes. N-Acyl amidines in particular can be used as a starting material for the synthesis of heterocycles and have several other applications. Here, we describe a fast and practical copper-catalyzed three-component reaction of aryl acetylenes, amines, and easily accessible 1,4,2-dioxazol-5-ones to N-acyl amidines, generating CO2 as the only byproduct. Transformation of the dioxazolones on the Cu catalyst generates acyl nitrenes that rapidly insert into the copper acetylide Cu-C bond rather than undergoing an undesired Curtius rearrangement. For nonaromatic dioxazolones, [Cu(OAc)(Xantphos)] is a superior catalyst for this transformation, leading to full substrate conversion within 10 min. For the direct synthesis of N-benzoyl amidine derivatives from aromatic dioxazolones, [Cu(OAc)(Xantphos)] proved to be inactive, but moderate to good yields were obtained when using simple copper(I) iodide (CuI) as the catalyst. Mechanistic studies revealed the aerobic instability of one of the intermediates at low catalyst loadings, but the reaction could still be performed in air for most substrates when using catalyst loadings of 5 mol %. The herein reported procedure not only provides a new, practical, and direct route to N-acyl amidines but also represents a new type of C-N bond formation.
