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D60400

Sigma-Aldrich

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

98%

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Synonym(s):
4,5-Dichloro-3,6-dioxo-1,4-cyclohexadiene-1,2-dicarbonitrile, DDQ
Empirical Formula (Hill Notation):
C8Cl2N2O2
CAS Number:
Molecular Weight:
227.00
Beilstein/REAXYS Number:
747939
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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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This Item
D71607137030714410
4,5-Dichloro-o-phenylenediamine 97%

D71607

4,5-Dichloro-o-phenylenediamine

3,5-Dichloro-1,2-diaminobenzene 97%

714410

3,5-Dichloro-1,2-diaminobenzene

reaction suitability

reagent type: oxidant

reaction suitability

-

reaction suitability

-

reaction suitability

-

Quality Level

200

Quality Level

-

Quality Level

-

Quality Level

-

mp

210-215 °C (dec.) (lit.)

mp

158-164 °C (lit.)

mp

130-132 °C (lit.)

mp

60-65 °C

form

powder

form

solid

form

powder

form

solid

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

-

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

signalword

Danger

hcodes

Hazard Classifications

Acute Tox. 3 Oral

supp_hazards

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges


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Customers Also Viewed

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)
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)
A novel method for the highly efficient synthesis of 1,2-benzisoxazoles under neutral conditions using the Ph3P/DDQ system
Iranpoor N, et al.
Tetrahedron Letters, 47, 8247-8247 (2006)
Ayse Kocabalkanli et al.
Farmaco (Societa chimica italiana : 1989), 57(12), 993-997 (2003-02-05)
Nucleosides have been of great interest since their strong antiviral activities were discovered. 1,3-Oxathiolane ring system has been known for many years, but it is in recent years that the ring has been used as the sugar ring in nucleoside
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)

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