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D60400

Sigma-Aldrich

2,3-Dichloro-5,6-dicyano-p-benzoquinone

98%

Synonym(s):

4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile, DDQ

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About This Item

Empirical Formula (Hill Notation):
C8Cl2N2O2
CAS Number:
84-58-2
Molecular Weight:
227.00
Beilstein:
747939
EC Number:
201-542-2
MDL number:
MFCD00001593
UNSPSC Code:
12352117
PubChem Substance ID:
24893996
NACRES:
NA.22

Quality Level

200

Assay

98%

form

powder

reaction suitability

reagent type: oxidant

mp

210-215 °C (dec.) (lit.)

storage temp.

2-8°C

SMILES string

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

InChI

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

InChI key

HZNVUJQVZSTENZ-UHFFFAOYSA-N

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Application

2,3-Dichloro-5,6-dicyano-p-benzoquinone (DDQ) can be used as:
  • A deprotecting reagent for a variety of compounds, such as thioacetals, acetals, and ketals.
  • An electron-transfer reagent for the synthesis of quinolines from imines and alkynes or alkenes.
  • An effective reagent for the benzylic and allylic C−H functionalization.
  • An oxidizing agent for the synthesis of functionalized furans and benzofurans.
  • A reagent with Ph3P in an efficient synthesis of 1,2-benzisoxazoles.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Supplementary Hazards

EUH029

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tetrahedron Letters, 47, 8247-8247 (2006)
Solvent-Free One-Step Photochemical Hydroxylation of Benzene Derivatives by the Singlet Excited State of 2, 3-Dichloro-5, 6-dicyano-p-benzoquinone Acting as a Super Oxidant.
Ohkubo K, et al.
Chemistry?A European Journal , 21(7), 2855-2861 (2015)
Deprotection of benzyl ethers using 2, 3-dichloro-5, 6-dicyano-p-benzoquinone (DDQ) under photoirradiation.
Rahim MA, et al.
Tetrahedron Letters, 46(43), 7307-7309 (2005)
Predictive model for oxidative C-H bond functionalization reactivity with 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone.
Morales-Rivera CA, et al.
Journal of the American Chemical Society, 139(49), 17935-17944 (2017)
DDQ-mediated formation of carbon? carbon bonds: Oxidation of imines
Bortolotti B, et al.
Tetrahedron, 49, 10157-10157 (1993)
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