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ALD00564

N-Hydroxytetrachlorophthalimide

Name: <I>N</I>-Hydroxytetrachlorophthalimide
Brand: ALDRICH

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₈HCl₄NO₃

CAS Number:

85342-65-0

Molecular Weight:

300.91

UNSPSC Code:

12352111

PubChem Substance ID:

329772721

NACRES:

NA.22

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

Related Categories

Oxidation Reagents

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

Pictograms

GHS06

Signal Word

Danger

Hazard Statements

H301

Precautionary Statements

P301 + P330 + P331 + P310

Hazard Classifications

Acute Tox. 3 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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

Tian Qin et al.

Science (New York, N.Y.), 352(6287), 801-805 (2016-04-23)

Alkyl carboxylic acids are ubiquitous in all facets of chemical science, from natural products to polymers, and represent an ideal starting material with which to forge new connections. This study demonstrates how the same activating principles used for decades to

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

Jie Wang et al.

Angewandte Chemie (International ed. in English), 55(33), 9676-9679 (2016-07-07)

A transformation analogous in simplicity and functional group tolerance to the venerable Suzuki cross-coupling between alkyl-carboxylic acids and boronic acids is described. This Ni-catalyzed reaction relies upon the activation of alkyl carboxylic acids as their redox-active ester derivatives, specifically N-hydroxy-tetrachlorophthalimide

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

Josep Cornella et al.

Journal of the American Chemical Society, 138(7), 2174-2177 (2016-02-03)

A new transformation is presented that enables chemists to couple simple alkyl carboxylic acids with aryl zinc reagents under Ni-catalysis. The success of this reaction hinges on the unique use of redox-active esters that allow one to employ such derivatives

Efficient metal-free aerobic oxidation of aromatic hydrocarbons utilizing aryl-tetrahalogenated N-hydroxyphthalimides and 1,4-diamino-2,3-dichloroanthraquinone.

Zhang Q, et al.

Journal of Chemical Technology and Biotechnology, 83(10), 1364-1369 (2008)

Articles

Electrochemical Allylic C–H Oxidation

Phil Baran develops ALD00564 reagent as a safe, cost-effective alternative for allylic oxidations and cross-coupling reactions.