Chinese name: 2,3 -dicyan-5,6-dichlorophenylhydrazine English name: 2,3-dicyano-5,6-dichlorobenzoquinone
MDL: MFCD000[1]01593
CASNo.:84-58-2
Molecular formula: C8Cl2N2O2
Molecular weight: 227.01
Main components: pure product
Melting point (°C): 213-215
Solubility: Soluble in benzene, acetic acid, slightly soluble in chloroform
Physical properties: bright yellow solid. The standard electrode potential is 1000 mV. Slightly soluble in water, soluble in benzene, dichloromethane, dioxane, acetic acid, soluble in tetrahydrofuran, ethyl acetate. It has been commercialized. It has a certain stability to the air, but it will release hydrogen cyanide when it meets water. It needs to be used in an anhydrous environment protected by inert gas.
Main use: DDQ is a highly active oxidant in organic synthesis, commonly used in dehydroaromatization and preparation of α,β-unsaturated carbonyl compounds. It was first used in the study of steroids in the 1960s because it is favored by a much stronger dehydrogenating agent than tetrachloro-p-benzoquinone. In the oxidation reaction, the hydrogen ions of the substrate are transferred to the DDQ, thereby dehydrogenating the substrate, and the DDQ is converted into tetrachlorotetracyanohydrin. The dehydrogenation reaction is related to the stability of the carbocation formed in the reaction and is particularly effective for compounds in which an ortho-stable group is present. DDQ also oxidizes active methylene and hydroxyl groups to carbonyl groups. Phenol is particularly sensitive to DDQ.
