2,3-Dichloro-5,6-dicyano-1,4-benzoquinone on:
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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (or DDQ) is the
:
"Like Neurons in the Brain": A Molecular Computer that Evolves
{{DEFAULTSORT:Dichloro-5, 6-Dicyano-1, 4-Benzoquinone, 2, 3- Nitriles Chlorobenzene compounds 1,4-Benzoquinones Oxidizing agents Reagents for organic chemistry
chemical reagent
In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...
with formula C6Cl2(CN)2O2. This oxidant is useful for the dehydrogenation of alcohols, phenols, and steroid ketones. DDQ decomposes in water, but is stable in aqueous mineral acid
A mineral acid (or inorganic acid) is an acid derived from one or more inorganic compounds, as opposed to organic acids which are acidic, organic compounds. All mineral acids form hydrogen ions and the conjugate base when dissolved in water.
Ch ...
.
Preparation
Synthesis of DDQ involves cyanation of chloranil. J. Thiele and F. Günther first reported a 6-step preparation in 1906. 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.Reactions
The reagent removes pairs of H atoms from organic molecules. The stoichiometry of its action is illustrated by the conversion oftetralin
Tetralin (1,2,3,4-tetrahydronaphthalene) is a hydrocarbon having the chemical formula C10H12. It is a partially hydrogenated derivative of naphthalene. It is a colorless liquid that is used as a hydrogen-donor solvent.
Production
Tetralin is pr ...
to naphthalene
Naphthalene is an organic compound with formula . It is the simplest polycyclic aromatic hydrocarbon, and is a white Crystal, crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 Parts-per notation ...
:
: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.
Dehydrogenation
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Aromatization
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Cross-Dehydrogenative Coupling
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:
Safety
DDQ reacts with water to release highly toxichydrogen cyanide
Hydrogen cyanide (formerly known as prussic acid) is a chemical compound with the chemical formula, formula HCN and structural formula . It is a highly toxic and flammable liquid that boiling, boils slightly above room temperature, at . HCN is ...
(HCN).
References
External links
"Like Neurons in the Brain": A Molecular Computer that Evolves
{{DEFAULTSORT:Dichloro-5, 6-Dicyano-1, 4-Benzoquinone, 2, 3- Nitriles Chlorobenzene compounds 1,4-Benzoquinones Oxidizing agents Reagents for organic chemistry