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A11879 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, 98%

CAS Number
84-58-2
Synonyms
2,3-Dichloro-5,6-dicyano-p-benzoquinone
4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile

Stock No. Size Price ($) Quantity Availability
A11879-09 10g 37.50
A11879-18 50g 126.00
A11879-30 250g 621.00
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2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, 98%

MDL
MFCD00001593
EINECS
201-542-2

Chemical Properties

Formula
C8Cl2N2O2
Formula Weight
227.01
Melting point
214-218°
Storage & Sensitivity
Moisture Sensitive. Store under Nitrogen. Ambient temperatures.
Solubility
Soluble in benzene, methanol, acetic acid and dioxane.Slightly soluble in chloroform,, dichloromethane.

Applications

2,3-Dichloro-5,6-dicyano-1,4-benzoquinone is used as a reagent for oxidative couplings and cyclization reactions and dehydrogenation of alcohols, phenols and steroid ketones. It is also used in the synthesis of 1,2-benzisoxazoles. It is a useful electron-transfer reagent for synthesis of quinolines from imines and alkynes or alkenes.

Notes

Store in a cool place. Incompatible with strong acids, strong bases, strong oxidizing agents and strong reducing agents.

Literature References

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):

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).

For a brief feature on uses of the reagent in synthesis, see: Synlett, 196 (2006).

Shehab, O. R.; Mansour, A. M. Sparfloxacin charge transfer complexes with 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone and tetracyanoquinodimethane: Molecular structures, spectral, and DFT studies. J. Mol. Struct. 2015, 1093, 186-194.

Uzochukwu, I. C.; Nzegbunam, S. O. Visible Spectrophotometric and Thermodynamic Studies of Diclofenac: Charge-Transfer Complexation with 2, 3 Dichloro-5, 6-dicyano, 1, 4-benzoquinone. Trop. J. Pharm. Res. 2015, 14 (3), 519-525.

GHS Hazard and Precautionary Statements

Hazard Statements: H301-H318

Toxic if swallowed. Causes serious eye damage.

Precautionary Statements: P264b-P270-P280-P301+P310-P305+P351+P338-P310-P330-P501c

Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Rinse mouth. Dispose of contents/ container to an approved waste disposal plant

Other References

Merck
14,3063
Beilstein
747939
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2926.90
TSCA
Yes
RTECS
GU4825000

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