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From Wikipedia, the free encyclopedia
(Redirected from Cucl2) Copper(II) chloride is the chemical compound with the formula CuCl2. This is a light brown solid, which slowly absorbs moisture to form a blue-green dihydrate. The copper(II) chlorides are some of the most common copper(II) compounds, after copper sulfate.
1 Structure 2 Properties and reactions 3 Preparation 3.1 Natural occurrence 4 Uses 4.1 Co-catalyst in Wacker Process 4.2 Chlorinations 4.3 Other organic synthetic applications 4.4 Niche uses 5 6 7 8 Safety References Further reading External links
IUPAC name Copper(II) chloride Copper dichloride Other names Cupric chloride
Identifiers CAS number 7447-39-4 , 10125-13-0 (dihydrate) PubChem 169664 ChemSpider 148374 UNII RTECS number
Cl[Cu]Cl [Cu+2].[Cl-].[Cl-] InChI InChI=1S/2ClH.Cu/h2*1H;/q;;+2/p-2
Anhydrous CuCl2 adopts a distorted cadmium iodide structure. In this motif, the copper centers are octahedral. Most copper(II) compounds exhibit distortions from idealized octahedral geometry due to the Jahn-Teller effect, which in this
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45 g/mol (anhydrous) 170. In CuCl2·2H2O.51 g/cm3 (dihydrate) Properties and reactions Aqueous solution prepared from copper(II) chloride contain a range of copper(II) complexes depending on Melting point 498 °C (anhydrous) 100 °C (dehydration of dihydrate) 993 °C (anhydrous.7 g/100 mL (25 °C) Structure Crystal distorted CdI2 structure structure Coordination Octahedral geometry Hazards MSDS Fischer Scientific (https://fscimage. the copper again adopts a highly distorted octahedral geometry.Wikipedia.6 g/100 mL (0 °C) water 75.386 g/cm3 (anhydrous) 2.. which bridge  asymmetrically to other Cu centers.48 g/mol (dihydrate) Appearance yellow-brown solid (anhydrous) blue-green solid (dihydrate) Density 3. more blue when lower on [Cl −]. Key: ORTQZVOHEJQUHG-UHFFFAOYSA-L InChI=1/2ClH. Solubility in 70.Cu/h2*1H.fishersci.org/wiki/Cucl2 case describes the localization of one d-electron into a molecular orbital that is strongly antibonding with respect to a pair of chloride ligands./q.+2/p-2 Key: ORTQZVOHEJQUHG-NUQVWONBAE Properties Molecular CuCl 2 formula Molar mass 134. concentration.. the Cu(II) centers being surrounded by two water ligands and four chloride ligands.+2/p-2/rCl2Cu /c1-3-2 Key: ORTQZVOHEJQUHG-LRIOHBSEAE InChI=1/2ClH.Cu/h2*1H. CuCl2·2H2O was used in the first electron paramagnetic resonance measurements by Yevgeny Zavoisky in  1944. Copper(II) chloride is paramagnetic. Of historical interest. decomp) Boiling point Aqueous solutions of "copper(II) chloride".htm) EU Not listed classification NFPA 704 2 Flash point 0 1 Non-flammable Related compounds 2 of 8 03/02/2011 10:35 AM . Greenish when high on [Cl −]. These species include blue color of 2+ and yellow or red color [Cu(H2O)6] of the halide complexes of the formula x−  [CuCl2+x ] ./q.com /msds/05625.Copper(II) chloride .wikipedia.and the presence of additional chloride ions. temperature. the free encyclopedia http://en.
org/wiki/Cucl2 It Copper(II) chloride dihydrate crystal Other anions Copper(II) fluoride Copper(II) bromide Other Copper(I) chloride cations Silver chloride Gold(III) chloride (what is this?) (verify) Except where noted otherwise. the free encyclopedia http://en.g. 100 kPa) Infobox references decomposes to CuCl and Cl2 at 1000 °C: 2 CuCl2 → 2 CuCl + Cl2 It reacts with HCl or other chloride sources to form complex ions: the red − 2−  CuCl3 . and they adopt a wide variety of structural types (Fig. triphenylphosphine).. iodide. 1).wikipedia. and cyanide as well as some tertiary amines cause reduction to give copper(I) 3 of 8 03/02/2011 10:35 AM . CuCl2 + 2 Cl− CuCl3 + Cl− − CuCl4 2− Some of these complexes can be crystallized from aqueous solution. and the yellow CuCl4 .Copper(II) chloride . data are given for materials in their standard state (at 25 °C.Wikipedia. Copper(II) hydroxide precipitates upon treating copper(II) chloride solutions with base: CuCl2 + 2 NaOH → Cu(OH)2 + 2 NaCl Copper(II) chloride also forms a variety of coordination complexes with ligands such as pyridine and triphenylphosphine oxide: CuCl2 + 2 C5H5N → [CuCl2(C5H5N)2] (tetragonal) CuCl2 + 2 (C6H5)3P=O → [CuCl2((C6H5)3P=O)2] (tetrahedral) However "soft" ligands such as phosphines (e.
Uses Co-catalyst in Wacker Process A major industrial application for copper(II) chloride is as a co-catalyst with palladium(II) chloride in the Wacker process.Copper(II) chloride . Anhydrous CuCl2 may be prepared directly by union of the elements.Wikipedia. completing the cycle. copper and chlorine. by  cooling in a CaCl2-ice bath.wikipedia. or copper(II) carbonate with hydrochloric acid. In this process. PdCl2 is reduced to Pd. ethene (ethylene) is converted to ethanal (acetaldehyde) using water and air. Preparation Copper(II) chloride is prepared commercially by the action of chlorination of copper: Cu + Cl2 + 2 H2O → CuCl2(H2O)2 It can also be generated by treatment of the hydroxide.org/wiki/Cucl2 complexes. During the reaction. a popular fungicide. Electrolysis of aqueous sodium chloride with copper electrodes produces (among other things) a blue-green foam that can be collected and converted to the hydrate. More common are mixed oxyhydroxide-chlorides like atacamite Cu2(OH)3Cl. Both are found near fumaroles. Natural occurrence Copper(II) chloride occurs naturally as the very rare mineral tolbachite and the dihydrate eriochalcite. oxide. To convert copper(II) chloride to copper(I) derivatives it is generally more convenient to reduce an aqueous solution with sulfur dioxide as the reductant: 2 CuCl2 + SO2 + 2 H2O → 2 CuCl + 2 HCl + H2SO4 Hydrolysis give the copper oxychloride. Air can then oxidize the resultant CuCl back to CuCl2. C2H4 + PdCl2 + H2O → CH3CHO + Pd + 2 HCl 4 of 8 03/02/2011 10:35 AM . 1. Cu2Cl(OH)3. the free encyclopedia http://en. and the CuCl2 serves to re-oxidize this back to PdCl2. CuCl2 may be purified by crystallization from hot dilute hydrochloric acid. arising among Cu ore beds oxidation zones in arid climate (also known from some altered slags).
e. Other organic synthetic applications Copper(II) chloride has a variety of specialized applications in the synthesis of  It effects chlorination of aromatic hydrocarbons. Pd + 2 CuCl2 → 2 CuCl + PdCl2 3. for  or aminoalcohols. It is able to chlorinate the  alpha position of carbonyl compounds: This reaction is performed in a polar solvent such as dimethylformamide (DMF). the free encyclopedia http://en. which accelerates the reaction. often performed in the presence of aluminium oxide. often in the presence of lithium chloride. 4 CuCl + 4 HCl + O2 → 4 CuCl2 + 2 H2O The overall process is: 2 C2H4 + O2 → 2 CH3CHO Chlorinations Copper(II) chloride catalyzes the chlorination in the production of vinyl chloride  and dichloroethane. as in this example (where deprotection to regenerate diols  TBDPS = tert-butyldiphenylsilyl): 5 of 8 03/02/2011 10:35 AM .1-binaphthol: Such compounds are intermediates in the synthesis of BINAP and its derivatives Copper(II) chloride dihydrate promotes the hydrolysis of acetonides. The latter process provides a high-yield route to 1.Copper(II) chloride .. CuCl2.this is organic compounds.org/wiki/Cucl2 2.wikipedia. i.Wikipedia. The major product can be directed to give either a quinone or a coupled product from oxidative  dimerization. can also oxidize phenols. in the presence of oxygen.
^ Greenwood. eds. http://books. 4. ISBN 0470258829. http://books. 167. copper chlorides.ch37 (http://dx.com /?id=l3F9yUSk-rgC&pg=PA3) . A. Inorg.Wikipedia.doi. Chemistry of the Elements (2nd Edn.google. ^ Wells. Oxford: Clarendon Press. In a flame test. Safety It is toxic and only concentrations below 5 ppm are allowed in drinking water by the US Environmental Protection Agency. Auxiliaries and Catalysts for C-C Bond Formation.com /?id=FldqbSffUMgC&pg=PA167) .com /?id=l3F9yUSk-rgC&pg=PA3.1002/9780470132401. Fairchild. ^ a b S.). Bertz.wikipedia. H.com /?id=PTXyS7Yj6zUC&pg=PA461) (6th ed. in Handbook of Reagents for Organic Synthesis. ^ W. Wiley.google.com /?id=FldqbSffUMgC&pg=PA167.. N. Niche uses Copper(II) chloride is also used in pyrotechnics as a blue/green coloring agent.google. doi:10. 6 of 8 03/02/2011 10:35 AM .org /10. ^ Naida S. Armarego. H.com /?id=PTXyS7Yj6zUC&pg=PA461. 3. E. 7. emit green-blue. Christina Li Lin Chai (2009-05-22) (Google Books excerpt). M. Mechanochemistry in Nanoscience and Minerals Engineering (http://books. ISBN 0-7506-3365-4.google. Gill et al. E. ISBN 1856175677. ISBN 0-19-855370-6. New York. L.org/wiki/Cucl2 CuCl2 also catalyses the free radical addition of sulfonyl chlorides to alkenes. 3. References 1. Denmark. Purification of Laboratory Chemicals (http://books. S.). A. pp. p. p.). ^ Peter Baláž (2008). John Wiley and Sons. 461. Volume 1: Reagents. Butterworth-Heinemann. Synth. ISBN 3540748547. 9: 136–142. F. (R. Coates. Oxford:ButterworthHeinemann. the free encyclopedia http://en. 6.ch37) . "Tetrahalo Complexes of Dipositive Metals in the First Transition Series". 220-3.google. (1997). Springer. ^ Marina Brustolon (2009). 1999.google. 2. (1984) Structural Inorganic Chemistry. N. http://books. & Earnshaw. pp. Electron paramagnetic resonance: a practitioner's toolkit (http://books. like all copper compounds. (1967). 5.1002%2F9780470132401.F.Copper(II) chloride . the alpha-chlorosulfone may then undergo elimination with base to give a vinyl  sulfone product.
Palakodety Radha. Earnshaw. 1992. 6. Greenwood.org /10.tetlet.1016/S0010-8545(00)80445-2 (http://dx. doi:10. Dayaker (2007).nih. 12. the free encyclopedia http://en. Journal of Organic Chemistry 68 (10): 4039–4045.Copper(II) chloride . E.08. J.org /10. USA. Chandra. p. 4.org /10. Oxford University Press. ISBN 0-8493-0471-7.doi. ISBN 0080379419 2. "Cupric Halide Halogenations". 1973. UK. Wiley-VCH. Oxford: Butterworth-Heinemann.org /10. Wells. "Chlorocuprates(II)". Wiley. New York.1016/j.. Alan. 7. Kusum L. Further reading 1. J. J. C. C.doi. Nicholls. "On the mechanism of the formation of s(−)-(1. New Jersey. M. doi:10. (1990). doi:10.doi. Coordination Chemistry Reviews 21 (2-3): 93–158. 5.org /10. Singh (2003). 1960.1016%2Fj.org/wiki/Cucl2 8. 7 of 8 03/02/2011 10:35 AM . (1997). doi:10. ^ Krishna. Complexes and First-Row Transition Elements. 8. Koppele. D. (+)-Deacetylboronolide.. Groenendijk. doi:10. D.Wikipedia.1002%2F14356007. ^ H. A. New York. ^ C.053 (http://dx. Tetrahedron Letters (Elsevier) 48: 7279–7282.1021/jo0269058 (http://dx.). Norman N.tetlet. Castro. March. Rahway.2007. Smith (1976).wikipedia. J. 1'-binaphthalene)-2. 7th edition. ^ Chandrasekhar.08. Owsley (1965).a07_567) 9.1016%2FS0010-8545%2800%2980445-2) . Advanced Organic Chemistry. Chemistry of the Elements (2nd ed. Fieser & Fieser Reagents for Organic Synthesis Volume 5. W. E. 10. M. and (+)-Dideacetylboronolide". Merck & Co. A. Jansen (1985).a07_567 (http://dx. 'Structural Inorganic Chemistry.doi. 3. 5th ed. G.org /10.1021%2Fjo01013a069) .1021%2Fjo0269058) . ^ J. London. and Vinod K. Tetrahedron 41: 3313.doi. 2005.1021/jo01013a069 (http://dx. Boca Raton: CRC Press.1002/14356007.doi. "Total Synthesis of (+)-Boronolide.ncbi. 1975.gov/pubmed /12737588) .nlm.2'-diol via copper(II)amine complexes". Gaughan..2007.053) .1016%2FS0040-4020%2801%299 6682-7) . Journal of Organic Chemistry 30: 587. 11. A. Wiley. 723. p158. Lide. Oxford. PMID 12737588 (http://www. David R. CRC handbook of chemistry and physics: a readyreference book of chemical and physical data. "A stereoselective total synthesis of (-)-andrachcinidine via an olefin cross-metathesis protocol". 4th ed.. 1984. "Copper Compounds" in Ullmann's Encyclopedia of Industrial Chemistry. L. The Merck Index. D. Macmillan Press. doi:10.Wayne Richardson. Weinheim.1016/S0040-4020(01)96682-7 (http://dx. G. F. Brussee.
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