Substance
ID:715229
Names and Identifiers
IUPAC Traditional name
4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile
IUPAC name
4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile
Synonyms
DDQ2,3-二氯-5,6-二氰基苯醌2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
Registration numbers
MDL Number
Beilstein Number
CAS Number
EC Number
Merck Index
Properties
Safety Information
GHS Precautionary statements
P264-P270-P301+P310-P321-P405-P501A
Safety Statements
7/8-20-36-45
Storage Warning
Moisture Sensitive
GHS Hazard statements
H301
European Hazard Symbols
Toxic (T)TSCA Listed
是
RTECS
GU4825000
Packing Group
II
GHS Pictograms
Acute toxicity (oral, dermal, inhalation), categories 1,2,3
Hazard Class
6.1
UN Number
UN3439
Risk Statements
25-29
Product Information
Purity
98+%
Physical Property
Melting Point
214-218°C
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
• Silyl and THP ethers are deprotected: J. Chem. Soc., Perkin 1, 2997 (1992); Synth. Commun., 25, 2373 (1995), respectively. Ethers of benzylic or allylic alcohols are oxidized to aldehydes, permitting the use of the methoxymethyl group as a masked aldehyde: Can. J. Chem., 67, 699 (1989). For cleavage of thioacetals to carbonyl groups, see: J. Org. Chem., 58, 7576 (1993); Chem. Lett., 965 (1994).
• Widely used dehydrogenation reagent, e.g. in aromatization reactions; review: Chem. Rev., 67, 153 (1967); 78, 317 (1978). For an example, see: Org. Synth. Coll., 6, 731 (1988). Dehydrogenation of chromanones to chromones and flavanones to flavones: Synthesis, 310 (1983); spirocyclohexenones to the corresponding cross-conjugated dienones: Org. Synth. Coll., 7, 473 (1990).
• Catalyzes formation of THP ethers from alcohols: Bull. Chem. Soc. Jpn., 65, 304 (1992), the isopropylidenation of carbohydrates with 2,2-Dimethoxypropane, A13810: Acta Chem. Scand., 47, 843 (1993); and C-N bond formation e.g. imines from arylamines and aldehydes (see also 1,2-Dianilinoethane, B23098), and, with 1 mole of DDQ, benzimidazole formation: Tetrahedron, 51, 5813 (1995):
• For a brief feature on uses of the reagent in synthesis, see: Synlett, 196 (2006).