ALD00564

N-Hydroxytetrachlorophthalimide

• Synonym(s): 4,5,6,7-Tetrachloro-2-hydroxy-1H-isoindole-1,3(2H)-dione, Tetrachloro-N-hydroxyphthalimide
• Empirical Formula (Hill Notation): C₈HCl₄NO₃
• CAS Number: 85342-65-0
• Molecular Weight: 300.91
• MDL number: MFCD29088000
• UNSPSC Code: 12352111
• PubChem Substance ID: 329772721
• NACRES: NA.22

Properties

• form: powder
• Quality Level: 100
• reaction suitability: reagent type: oxidant
• SMILES string: O=C1N(O)C(C2=C(Cl)C(Cl)=C(Cl)C(Cl)=C21)=O
• InChI: 1S/C8HCl4NO3/c9-3-1-2(4(10)6(12)5(3)11)8(15)13(16)7(1)14/h16H
• InChI key: UTRBHXSKVVPTLY-UHFFFAOYSA-N

Description

General description

N-Hydroxytetrachlorophthalimide (TCNHPI) is an aryl-tetrahalogenated N-hydroxyphthalimide derivative. In combination with 1,4-diamino-2,3-dichloroanthraquinone (DADCAQ), it forms an efficient catalytic system for the oxidation of aromatic hydrocarbons using molecular oxygen under metal-free and aerobic conditions.

Application

New reagent enabling the electrochemical allylic C-H oxidation reaction developed by the Baran group. This method provides a scalable and sustainable alternative to current strategies based on toxic reagents or precious metals.

Other Notes

Electrochemical Allylic C–H Oxidation with N-Hydroxytetrachlorophthalimide (TCNHPI)

Scalable and sustainable electrochemical allylic C–H oxidation

A general alkyl-alkyl cross-coupling enabled by redox-active esters and alkylzinc reagents

Nickel-Catalyzed Cross-Coupling of Redox-Active Esters with Boronic Acids

Practical Ni-Catalyzed Aryl-Alkyl Cross-Coupling of Secondary Redox-Active Esters

Safety Information

• pictograms: GHS06
• signalword: Danger
• hcodes: H301
• pcodes: P301 + P330 + P331 + P310
• Hazard Classifications: Acute Tox. 3 Oral
• 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