"DDQ" redirects here. For the Australian television station, see RTQ.
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,[3] phenols,[4] and steroid ketones.[5] DDQ decomposes in water, but is stable in aqueous mineral acid.[6]
Synthesis of DDQ involves cyanation of chloranil. J. Thiele and F. Günther first reported a 6-step preparation in 1906.[7] 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.[8]
ReactionsEdit
The reagent removes pairs of H atoms from organic molecules. The stoichiometry of its action is illustrated by the conversion of tetralin to naphthalene:
DDQ reacts with water to release highly toxic hydrogen cyanide (HCN).[citation needed] A low-temperature and weakly acidic environment increases the stability of DDQ.
ReferencesEdit
^2,3-Dichloro-5,6-dicyano-p-benzoquinone at Sigma-Aldrich
^Braude, E. A.; Linstead, R. P.; Wooldridge, K. R. H. (1956). "593. Hydrogen Transfer. Part IX The Selective Dehydrogenation of Unsaturated Alcohols by High-potential Quinones". Journal of the Chemical Society (Resumed). 1956: 3070–3074. doi:10.1039/JR9560003070.
^Becker, H. D. (1965). "Quinone Dehydrogenation. I. Oxidation of Monohydric Phenols". Journal of Organic Chemistry. 30 (4): 982–989. doi:10.1021/jo01015a006.
^Turner, A. B.; Ringold, H. J. (1967). "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: 1720–1730. doi:10.1039/J39670001720.
^Buckle, Derek R.; Collier, Steven J.; McLaws, Mark D. (2005). "2,3-Dichloro-5,6-dicyano-1,4-benzoquinone". e-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rd114.pub2.
^Thiele, J.; Günther, F. (1906). "Ueber Abkömmlinge des Dicyanhydrochinons". Justus Liebig's Annalen der Chemie. 349 (1): 45–66. doi:10.1002/jlac.19063490103.
^Walker, D.; Waugh, T. D. (1965). "2,3-Dichloro-5,6-Dicyanobenzoquinone (DDQ). A New Preparation". The Journal of Organic Chemistry. 30 (9): 3240. doi:10.1021/jo01020a529.
^Rathore, Rajendra; Kochi, Jay K. (2000), "Donor/acceptor organizations and the electron-transfer paradigm for organic reactivity", Advances in Physical Organic Chemistry, Elsevier, pp. 193–318, doi:10.1016/s0065-3160(00)35014-6, ISBN9780120335350
^Brown, W.; Turner, A. B. (1971). "Application of High-potential Quinones. 7. Synthesis of Steroidal Phenanthrenes by Double Methyl Migration". Journal of the Chemical Society C: Organic. 1971: 2566–2572. doi:10.1039/J39710002566. PMID 5167256.
^Zhang, Y.; Li, C. J. (2006). "DDQ-Mediated Direct Cross-Dehydrogenative-Coupling (CDC) between Benzyl Ethers and Simple Ketones". Journal of the American Chemical Society. 128 (13): 4242–4243. doi:10.1021/ja060050p. PMID 16568995.
External linksEdit
October 18, 2023
dichloro, dicyano, benzoquinone, redirects, here, australian, television, station, chemical, reagent, with, formula, c6cl2, this, oxidant, useful, dehydrogenation, alcohols, phenols, steroid, ketones, decomposes, water, stable, aqueous, mineral, acid, namespre. DDQ redirects here For the Australian television station see RTQ 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 3 phenols 4 and steroid ketones 5 DDQ decomposes in water but is stable in aqueous mineral acid 6 2 3 Dichloro 5 6 dicyano 1 4 benzoquinone 1 NamesPreferred IUPAC name 4 5 Dichloro 3 6 dioxocyclohexa 1 4 diene 1 2 dicarbonitrile 2 Other names 2 3 Dichloro 5 6 dicyano p benzoquinone4 5 Dichloro 3 6 dioxo 1 4 cyclohexadiene 1 2 dicarbonitrileDichlorodicyanobenzoquinoneIdentifiersCAS Number 84 58 2 Y3D model JSmol Interactive imageAbbreviations DDQChemSpider 6517 YECHA InfoCard 100 001 402EC Number 201 542 2PubChem CID 6775RTECS number GU4825000UNII 1H5KD39UH7 YCompTox Dashboard EPA DTXSID7052577InChI InChI 1S C8Cl2N2O2 c9 5 6 10 8 14 4 2 12 3 1 11 7 5 13 YKey HZNVUJQVZSTENZ UHFFFAOYSA N YInChI 1 C8Cl2N2O2 c9 5 6 10 8 14 4 2 12 3 1 11 7 5 13Key HZNVUJQVZSTENZ UHFFFAOYALSMILES ClC 1C O C C N C C N C O C 1ClPropertiesChemical formula C 8Cl 2N 2O 2Molar mass 227 00 g mol 1Appearance yellow to orange powderDensity 1 7g cm3Melting point 210 215 C 410 419 F 483 488 K decomposes Boiling point 301 8 C 575 2 F 575 0 K at 760mmHgSolubility in water reactsHazardsGHS labelling PictogramsSignal word DangerHazard statements H301Precautionary statements P264 P270 P301 P310 P321 P330 P405 P501Flash point 136 3 C 277 3 F 409 4 K Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Contents 1 Preparation 2 Reactions 2 1 Dehydrogenation 2 2 Aromatization 2 3 Cross Dehydrogenative Coupling 3 Safety 4 References 5 External linksPreparation EditSynthesis of DDQ involves cyanation of chloranil J Thiele and F Gunther first reported a 6 step preparation in 1906 7 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 8 Reactions EditThe 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 C10H8The 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 9 Dehydrogenation Edit nbsp Aromatization Edit nbsp 10 Cross Dehydrogenative Coupling Edit nbsp 11 Safety EditDDQ reacts with water to release highly toxic hydrogen cyanide HCN citation needed A low temperature and weakly acidic environment increases the stability of DDQ References Edit 2 3 Dichloro 5 6 dicyano p benzoquinone at Sigma Aldrich Nomenclature of Organic Chemistry IUPAC Recommendations and Preferred Names 2013 Blue Book Cambridge The Royal Society of Chemistry 2014 p 50 doi 10 1039 9781849733069 FP001 ISBN 978 0 85404 182 4 Braude E A Linstead R P Wooldridge K R H 1956 593 Hydrogen Transfer Part IX The Selective Dehydrogenation of Unsaturated Alcohols by High potential Quinones Journal of the Chemical Society Resumed 1956 3070 3074 doi 10 1039 JR9560003070 Becker H D 1965 Quinone Dehydrogenation I Oxidation of Monohydric Phenols Journal of Organic Chemistry 30 4 982 989 doi 10 1021 jo01015a006 Turner A B Ringold H J 1967 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 1720 1730 doi 10 1039 J39670001720 Buckle Derek R Collier Steven J McLaws Mark D 2005 2 3 Dichloro 5 6 dicyano 1 4 benzoquinone e EROS Encyclopedia of Reagents for Organic Synthesis doi 10 1002 047084289X rd114 pub2 Thiele J Gunther F 1906 Ueber Abkommlinge des Dicyanhydrochinons Justus Liebig s Annalen der Chemie 349 1 45 66 doi 10 1002 jlac 19063490103 Walker D Waugh T D 1965 2 3 Dichloro 5 6 Dicyanobenzoquinone DDQ A New Preparation The Journal of Organic Chemistry 30 9 3240 doi 10 1021 jo01020a529 Rathore Rajendra Kochi Jay K 2000 Donor acceptor organizations and the electron transfer paradigm for organic reactivity Advances in Physical Organic Chemistry Elsevier pp 193 318 doi 10 1016 s0065 3160 00 35014 6 ISBN 9780120335350 Brown W Turner A B 1971 Application of High potential Quinones 7 Synthesis of Steroidal Phenanthrenes by Double Methyl Migration Journal of the Chemical Society C Organic 1971 2566 2572 doi 10 1039 J39710002566 PMID 5167256 Zhang Y Li C J 2006 DDQ Mediated Direct Cross Dehydrogenative Coupling CDC between Benzyl Ethers and Simple Ketones Journal of the American Chemical Society 128 13 4242 4243 doi 10 1021 ja060050p PMID 16568995 External links Edit Like Neurons in the Brain A Molecular Computer that Evolves Retrieved from https en wikipedia org w index php title 2 3 Dichloro 5 6 dicyano 1 4 benzoquinone amp oldid 1172735902, wikipedia, wiki, book, books, library,
