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ALD00564

N-羟基四氯邻苯二甲酰亚胺

Name: <I>N</I>-羟基四氯邻苯二甲酰亚胺
Brand: ALDRICH

别名:

4,5,6,7-四氯-2-羟基-1H-异吲哚-1,3(2H)-二酮, 四氯-N-羟基邻苯二甲酰亚胺

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About This Item

经验公式（希尔记法）:

C₈HCl₄NO₃

CAS号:

85342-65-0

分子量:

300.91

UNSPSC代码:

12352111

PubChem化学物质编号:

329772721

NACRES:

NA.22

形式

powder

质量水平

100

反应适用性

reagent type: oxidant

SMILES字符串

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

一般描述

N-羟基四氯邻苯二甲酰亚胺（TCNHPI）是一种芳基-四卤代N-羟基邻苯二甲酰亚胺衍生物。与1,4-二氨基-2,3-二氯蒽醌（DADCAQ）组合可形成一种有效的催化系统，用于在无金属和有氧条件下利用分子氧实现芳烃的氧化反应。

应用

新试剂能够实现Baran团队开发的电化学烯丙基C-H氧化反应。该方法为当前基于有毒试剂或贵金属的方法提供了一种可扩展且可持续的替代方案。

其他说明

与N-羟基四氯邻苯二甲酰亚胺（TCNHPI）发生电化学烯丙基C-H氧化反应

可扩展且可持续的电化学烯丙基C-H氧化反应

利用氧化还原活性酯和烷基锌试剂实现一般烷基-烷基交叉偶联

镍催化的氧化还原活性酯与硼酸的交叉偶联

镍催化的二级氧化还原活性酯的芳基-烷基交叉偶联

象形图

GHS06

警示用语：

Danger

危险声明

H301

预防措施声明

P301 + P330 + P331 + P310

危险分类

Acute Tox. 3 Oral

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

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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)

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

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

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