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ALD00564 Aldrich

N-Hydroxytetrachlorophthalimide

Synonym: 4,5,6,7-Tetrachloro-2-hydroxy-1H-isoindole-1,3(2H)-dione, Tetrachloro-N-hydroxyphthalimide

  • CAS Number 85342-65-0

  • Empirical Formula (Hill Notation) C8HCl4NO3

  • Molecular Weight 300.91

  •  PubChem Substance ID 329772721

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Properties

Related Categories Chemical Synthesis, Other Oxidizing Agents, Oxidizing Agents, Perchlorates, Synthetic Reagents More...
InChI Key   UTRBHXSKVVPTLY-UHFFFAOYSA-N
form   powder

Description

Packaging

1, 10 g in glass bottle

50 g in poly bottle

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.

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.

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

Price and Availability

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
3

Documents

Certificate of Analysis

Protocols & Articles

Articles

Baran Group - Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Baran Group - Professor Product Portal
Keywords: Building blocks, Fluorinations, Oxidations, Pharmaceutical

Synthetic Reagents Electrochemical Allylic Oxidation (TCNHPI)

Professor Phil Baran and coworkers have developed a new reagent, N-Hydroxytetrachlorophthalimide (ALD00564), which provides a cheap, scalable, and safe synthetic alternative to highly used transforma...
Keywords: Catalysis, Coupling reactions, Cross couplings, Deprotonations, Natural product synthesis, Oxidations, Suzuki coupling

Peer-Reviewed Papers
15

References

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