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ALD00564

Sigma-Aldrich

N-Hydroxytetrachlorophthalimide

Synonyma:

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

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About This Item

Empirický vzorec (Hillův zápis):
C8HCl4NO3
Číslo CAS:
85342-65-0
Molekulová hmotnost:
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

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

Skull and crossbones
GHS06

signalword

Danger

hcodes

H301

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

Osvědčení o analýze (COA)

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Navštívit knihovnu dokumentů

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
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
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)

Sortimentní položky

Electrochemical Allylic C–H Oxidation

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

Související obsah

Baran Group – Professor Product Portal

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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