Home > Compound List > Product Information
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone_Molecular_structure_CAS_84-58-2)
Click picture or here to close

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

Catalog No. A11879 Name Alfa Aesar
CAS Number 84-58-2 Website
M. F. C8Cl2N2O2 Telephone
M. W. 227.0038 Fax
Purity 98+% Email
Storage Chembase ID: 77210

SYNONYMS

Title
2,3-二氯-5,6-二氰基苯醌
IUPAC name
4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile
IUPAC Traditional name
4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile
Synonyms
DDQ

DATABASE IDS

CAS Number 84-58-2
Merck Index 143063
MDL Number MFCD00001593
EC Number 201-542-2
Beilstein Number 747939

PROPERTIES

Purity 98+%
Melting Point 214-218°C
GHS Pictograms GHS06
GHS Hazard statements H301
European Hazard Symbols Toxic Toxic (T)
GHS Precautionary statements P264-P270-P301+P310-P321-P405-P501A
Risk Statements 25-29
RTECS GU4825000
Safety Statements 7/8-20-36-45
Storage Warning Moisture Sensitive
TSCA Listed
Hazard Class 6.1
UN Number UN3439
Packing Group II

DETAILS

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).