D60400

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: 84-58-2
• Molecular Weight: 227.00
• Beilstein/REAXYS Number: 747939
• EC Number: 201-542-2
• MDL number: MFCD00001593
• UNSPSC Code: 12352117
• PubChem Substance ID: 24893996
• NACRES: NA.22

Properties

• 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

Description

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.

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H301
• pcodes: P264 - P270 - P301 + P310 - P405 - P501
• Hazard Classifications: Acute Tox. 3 Oral
• supp_hazards: EUH029
• 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