2,3-dichloro-5,6-dicyanobenzoquinone
Also known as DDQ, dichlorodicyanobenzoquinone
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, phenols, and steroid ketones. DDQ decomposes in water, but is stable in aqueous mineral acid.
Wikidata facts
- Mass
- 225.934
Show 4 more facts
- melting point
- 215.0
- chemical formula
- C₈Cl₂N₂O₂
- Commons category
- Dichlorodicyanobenzoquinone
- canonical SMILES
- C(#N)C1=C(C(=O)C(=C(C1=O)Cl)Cl)C#N
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Article
8 sectionsContents
- Preparation
- Reactions
- Dehydrogenation
- Aromatization
- Cross-Dehydrogenative Coupling
- Safety
- References
- External links
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, phenols, and steroid ketones. DDQ decomposes in water, but is stable in aqueous mineral acid.
==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.