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Key Documents

ALD00564

Sigma-Aldrich

N-Hydroxytetrachlorophthalimide

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C8HCl4NO3
Número CAS:
Peso molecular:
300.91
Código UNSPSC:
12352111
ID de substância PubChem:
NACRES:
NA.22

forma

powder

Nível de qualidade

adequação da reação

reagent type: oxidant

cadeia de caracteres SMILES

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

chave InChI

UTRBHXSKVVPTLY-UHFFFAOYSA-N

Descrição geral

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.

Aplicação

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.

Pictogramas

Skull and crossbones

Palavra indicadora

Danger

Frases de perigo

Declarações de precaução

Classificações de perigo

Acute Tox. 3 Oral

Código de classe de armazenamento

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable


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Os clientes também visualizaram

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
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
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)

Artigos

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 transformations like allylic oxidations, as well as Negishi and Suzuki–Miyaura type cross-coupling reactions.

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