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

{{Redirect|DDQ|the Australian television station|RTQ}}

{{Chembox

|Watchedfields = changed

|verifiedrevid = 477190823

|Reference =[https://www.sigmaaldrich.com/US/en/product/aldrich/d60400 2,3-Dichloro-5,6-dicyano-p-benzoquinone] at Sigma-Aldrich

|ImageFileL1 = Dichlorodicyanobenzoquinone.svg

|ImageSizeL1 = 120

|ImageAltL1 = Structural formula of dichlorodicyanobenzoquinone

|ImageFileR1 = Dichlorodicyanobenzoquinone 3D spacefill.png

|ImageSizeR1 = 130

|ImageAltR1 = Space-filling model of the dichlorodicyanobenzoquinone molecule

|ImageFile2= DDQpowder.jpg

|PIN = 4,5-Dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 50 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}

|OtherNames = {{unbulleted list

|2,3-Dichloro-5,6-dicyano-p-benzoquinone

|4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile

|Dichlorodicyanobenzoquinone}}

|Section1={{Chembox Identifiers

|Abbreviations = DDQ

|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

|ChemSpiderID = 6517

|InChI = 1/C8Cl2N2O2/c9-5-6(10)8(14)4(2-12)3(1-11)7(5)13

|InChIKey = HZNVUJQVZSTENZ-UHFFFAOYAL

|StdInChI_Ref = {{stdinchicite|correct|chemspider}}

|StdInChI = 1S/C8Cl2N2O2/c9-5-6(10)8(14)4(2-12)3(1-11)7(5)13

|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|StdInChIKey = HZNVUJQVZSTENZ-UHFFFAOYSA-N

|CASNo_Ref = {{cascite|correct|CAS}}

|CASNo = 84-58-2

|UNII_Ref = {{fdacite|correct|FDA}}

|UNII = 1H5KD39UH7

|PubChem =6775

|RTECS = GU4825000

|EINECS = 201-542-2

|SMILES = ClC=1C(=O)C(\C#N)=C(\C#N)C(=O)C=1Cl

}}

|Section2={{Chembox Properties

|C=8 | Cl=2 | N=2 | O=2

|Appearance = yellow to orange powder

|Density = 1.7g/cm3

|MeltingPtC = 210 - 215

|MeltingPt_notes = (decomposes)

|BoilingPtC = 301.8

|BoilingPt_notes = at 760mmHg

|Solubility = reacts}}

|Section3={{Chembox Hazards

|FlashPtC = 136.3

|GHSPictograms = {{GHS06}}

|GHSSignalWord = Danger

|HPhrases = {{H-phrases|301}}

|PPhrases = {{P-phrases|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,{{cite journal | journal = Journal of the Chemical Society (Resumed) |author1=Braude, E. A. |author2=Linstead, R. P. |author3=Wooldridge, K. R. H. | title = 593. Hydrogen Transfer. Part IX The Selective Dehydrogenation of Unsaturated Alcohols by High-potential Quinones | year = 1956 | volume = 1956 | pages = 3070–3074 | doi = 10.1039/JR9560003070}} phenols,{{cite journal | author = Becker, H. D. | title = Quinone Dehydrogenation. I. Oxidation of Monohydric Phenols | journal = Journal of Organic Chemistry | year = 1965 | volume = 30 | issue = 4 | pages = 982–989 | doi = 10.1021/jo01015a006 }} and steroid ketones.{{cite journal|author1=Turner, A. B. |author2=Ringold, H. J. | title = Applications of High-potential Quinones. Part I. The Mechanism of Dehydrogenation of Steroidal Ketones by 2,3-Dichloro-5,6-Dicyanobenzoquinone | journal = Journal of the Chemical Society C: Organic | year = 1967 | volume = 1967 | pages = 1720–1730 | doi = 10.1039/J39670001720}} DDQ decomposes in water, but is stable in aqueous mineral acid.{{cite encyclopedia|first1=Derek R.|last1=Buckle|first2=Steven J.|last2=Collier|first3=Mark D.|last3=McLaws|title=2,3-Dichloro-5,6-dicyano-1,4-benzoquinone|encyclopedia=e-EROS Encyclopedia of Reagents for Organic Synthesis|year= 2005|doi= 10.1002/047084289X.rd114.pub2|isbn=0471936235 }}