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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
Empirical Formula (Hill Notation):
C8Cl2N2O2
CAS Number:
Molecular Weight:
227.00
Beilstein:
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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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.

Packaging

5, 10, 100 g in glass bottle

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral

Supplementary Hazards

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

Certificate of Analysis

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Certificate of Origin

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