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ALD00564

Sigma-Aldrich

N-Hydroxytetrachlorophthalimide

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:
Molecular Weight:
300.91
UNSPSC Code:
12352111
PubChem Substance ID:
NACRES:
NA.22

form

powder

Quality Level

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

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.

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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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)

Articles

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.

Related Content

The Baran Group works with Sigma-Aldrich in providing a portfolio of zinc-based reagents promoting difluoromethylation, trifluoromethylation, trifluoroethylation and isopropylation of aryl and heteroaryl motifs. Baran’s lab has also helped introduce a portable desaturase (Tz0Cl), which promotes the installation of alcohol and amine groups and leaves behind a highly useful tosyl group for further transformations.

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