2,3-Dichloro-5,6-dicyano-1,4-benzoquinone

DDQ the Australian television station RTQ changed 477190823 2,3-Dichloro-5,6-dicyano-p-benzoquinone at Sigma-Aldrich Dichlorodicyanobenzoquinone.svg 120 Structural formula of dichlorodicyanobenzoquinone Dichlorodicyanobenzoquinone 3D spacefill.png 130 Space-filling model of the dichlorodicyanobenzoquinone molecule DDQpowder.jpg 4,5-Dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) The Royal Society of Chemistry 2014 Cambridge 50 10.1039/9781849733069-FP001 978-0-85404-182-4 2,3-Dichloro-5,6-dicyano-p-benzoquinone 4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile Dichlorodicyanobenzoquinone DDQ correct chemspider 6517 1/C8Cl2N2O2/c9-5-6(10)8(14)4(2-12)3(1-11)7(5)13 HZNVUJQVZSTENZ-UHFFFAOYAL correct chemspider 1S/C8Cl2N2O2/c9-5-6(10)8(14)4(2-12)3(1-11)7(5)13 correct chemspider HZNVUJQVZSTENZ-UHFFFAOYSA-N correct CAS 84-58-2 correct FDA 1H5KD39UH7 6775 GU4825000 201-542-2 ClC=1C(=O)C(\C#N)=C(\C#N)C(=O)C=1Cl 8 2 2 2 yellow to orange powder 1.7g/cm3 210 - 215 (decomposes) 301.8 at 760mmHg reacts 136.3 06 Danger 301 264 270 301+310 321 330 405 501 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (or DDQ) is the chemical reagent with formula C6Cl2(CN)2O2. This oxidant is useful for the dehydrogenation of alcohols, Journal of the Chemical Society (Resumed) Braude, E. A. Linstead, R. P. Wooldridge, K. R. H. 593. Hydrogen Transfer. Part IX The Selective Dehydrogenation of Unsaturated Alcohols by High-potential Quinones 1956 1956 3070–3074 10.1039/JR9560003070 phenols, Becker, H. D. Quinone Dehydrogenation. I. Oxidation of Monohydric Phenols Journal of Organic Chemistry 1965 30 4 982–989 10.1021/jo01015a006 and steroid ketones.Turner, A. B. Ringold, H. J. Applications of High-potential Quinones. Part I. The Mechanism of Dehydrogenation of Steroidal Ketones by 2,3-Dichloro-5,6-Dicyanobenzoquinone Journal of the Chemical Society C: Organic 1967 1967 1720–1730 10.1039/J39670001720 DDQ decomposes in water, but is stable in aqueous mineral acid.Derek R. Buckle Steven J. Collier Mark D. McLaws 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone e-EROS Encyclopedia of Reagents for Organic Synthesis 2005 10.1002/047084289X.rd114.pub2 0471936235 Preparation Synthesis of DDQ involves cyanation of chloranil. J. Thiele and F. Günther first reported a 6-step preparation in 1906. Justus Liebig's Annalen der Chemie Thiele, J. Günther, F. Ueber Abkömmlinge des Dicyanhydrochinons 1906 349 1 45–66 10.1002/jlac.19063490103 https://zenodo.org/record/1427563 The substance did not receive interest until its potential as a dehydrogenation agent was discovered. A single-step chlorination from 2,3-dicyanohydroquinone was reported in 1965.Walker, D. Waugh, T. D. 2,3-Dichloro-5,6-Dicyanobenzoquinone (DDQ). A New Preparation The Journal of Organic Chemistry 1965 30 9 3240 10.1021/jo01020a529 Reactions The reagent removes pairs of H atoms from organic molecules. The stoichiometry of its action is illustrated by the conversion of tetralin to naphthalene: 2 C6Cl2(CN)2O2 + C10H12 → 2 C6Cl2(CN)2(OH)2 + C10H8 The resulting hydroquinone is poorly soluble in typical reaction solvents (dioxane, benzene, alkanes), which facilitates workup. Solutions of DDQ in benzene are red, due to the formation of a charge-transfer complex.Rathore Rajendra Donor/acceptor organizations and the electron-transfer paradigm for organic reactivity 2000 Advances in Physical Organic Chemistry 193–318 Elsevier 10.1016/s0065-3160(00)35014-6 9780120335350 Kochi Jay K. Dehydrogenation 400px Aromatization 400pxBrown, W. Turner, A. B. Application of High-potential Quinones. 7. Synthesis of Steroidal Phenanthrenes by Double Methyl Migration Journal of the Chemical Society C: Organic 1971 1971 2566–2572 10.1039/J39710002566 5167256 Cross-Dehydrogenative Coupling 400px Zhang, Y. Li, C. J. DDQ-Mediated Direct Cross-Dehydrogenative-Coupling (CDC) between Benzyl Ethers and Simple Ketones Journal of the American Chemical Society 2006 128 13 4242–4243 10.1021/ja060050p 16568995 2006JAChS.128.4242Z Safety DDQ reacts with water to release highly toxic hydrogen cyanide (HCN). References External links "Like Neurons in the Brain": A Molecular Computer that Evolves Category:Nitriles Category:Chlorobenzene compounds Category:1,4-Benzoquinones Category:Oxidizing agents Category:Reagents for organic chemistry