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ALD00564

Sigma-Aldrich

N-Hydroxytetrachlorophthalimide

Sinonimo/i:

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

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1 G
CHF 32.90
10 G
CHF 98.60
50 G
CHF 433.00

CHF 32.90

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Cambia visualizzazione
1 G
CHF 32.90
10 G
CHF 98.60
50 G
CHF 433.00

About This Item

Formula empirica (notazione di Hill):
C8HCl4NO3
Numero CAS:
85342-65-0
Peso molecolare:
300.91
Numero MDL:
MFCD29088000
Codice UNSPSC:
12352111
ID PubChem:
329772721
NACRES:
NA.22

CHF 32.90

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Stato

powder

Livello qualitativo

100

Impiego in reazioni chimiche

reagent type: oxidant

Stringa SMILE

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
UTRBHXSKVVPTLY-UHFFFAOYSA-N

Categorie correlate

Descrizione generale

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.[1]

Applicazioni

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.

Altre note

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

Pittogrammi

Skull and crossbones
GHS06

Avvertenze

Danger

Indicazioni di pericolo

H301

Consigli di prudenza

P301 + P330 + P331 + P310

Classi di pericolo

Acute Tox. 3 Oral

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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Certificati d'analisi (COA)

Lot/Batch Number
0000388816
0000388815
0000388817
0000388817
0000388816

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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)
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
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

Articoli

Electrochemical Allylic C–H Oxidation

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

Contenuto correlato

Baran Group – Prof. Product Portal

Baran Group offers zinc-based reagents for versatile transformations in organic synthesis.

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