CAS 84-58-2|4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile|4,5-dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile|2,3-DICHLORO-5,6-DICYANOQUINONE|1,2-Dichloro-4,5-dicyano-3,6-dio...

General Information

Structure

Molecular Formula

C₈Cl₂N₂O₂

Molecular Mass

227.0038

Exact Mass

225.93368261

Charge

InChI

InChI=1S/C8Cl2N2O2/c9-5-6(10)8(14)4(2-12)3(1-11)7(5)13

InChIKey

HZNVUJQVZSTENZ-UHFFFAOYSA-N

Canonic Smiles

N#CC1=C(C#N)C(=O)C(=C(C1=O)Cl)Cl

Isomeric Smiles

ClC1=C(C(=O)C(=C(C1=O)C#N)C#N)Cl

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

1.4257357

LogD (pH = 7.4)

1.4257357

Log P

1.4257357

Molar Refractivity

50.7186

Polarizability

18.073162

Polar Surface Area

81.72

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

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

2,3-DICHLORO-5,6-DICYANOQUINONE4,5-Dichloro-3,6-dioxocyclohexa-1,4-diene-1,2-dicarbonitrile2,3-Dichloro-5,6-dicyano-1,4-benzoquinone1,2-Dichloro-4,5-dicyano-3,6-dioxocyclohexa-1,4-diene2,3-Dichloro-5,6-dicyano-p-benzoquinone2,3-二氯-5,6-二氰基对苯醌4,5-二氯-3,6-二氧-1,4-环己二烯-1,2-二甲腈DDQ4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile* 2,3-Dichloro-5,6-dicyano-p-benzoquinone* 4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile* Dichlorodicyanobenzoquinone2,3-DICHLORO-5,6-DICYANO-1,4-BENZOQUINONEDichlorodicyano-p-benzoquinone1,2-Dichloro-4,5-dicyano-p-benzoquinoneNSC 401087Dicyanodichloroquinone2,3-Dichloro-5,6-dicyano-p-quinone2,3-Dichloro-5,6-dicyanobenzoquinone2,3-Chloro-5,6-dicyanoquinone2,3-Dichloro-5,6-dicyano-1,4-benzoquinone2,3-二氯-5,6-二氰基苯醌2,3-Dichloro-5,6-dicyano-p-benzoquinone

Names and Identifiers

Registration numbers

EC Number

Merck Index

Beilstein Number

MDL Number

CAS Number

PubChem SID

2486186716204208324893996

Wikipedia Title

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

PubChem CID

6775

Chemspider ID

6517

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02150864

Orange-yellow crystals.
Dehydrogenation reagent. Also used as a spray reagent for carbazoles.

05209966

MP Biomedicals Rare Chemical collection

Wikipedia

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

Sigma Aldrich

D60400

Application
Used with Ph3P in an efficient synthesis of 1,2-benzisoxazoles.1
Versatile deprotection reagent for a variety of compounds, such as thioacetals, acetals, and ketals. Useful electron-transfer reagent for synthesis of quinolines from imines and alkynes or alkenes.
Packaging
5, 10, 100 g in glass bottle

35680

Other Notes
Reagent for the dehydrogenation of hydroaromatic compounds1; Reagent for the mild cleavage of ether-type protecting groups2,3,4

TRC

D434110

An oxidizing agent, especially in steroid synthesis.

Molecule Details

References

PubChem Literature

From Data Sources

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

• 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).

• 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):

• 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).

References

Bioactivity

PubChem BioAssay

Bioactivity