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1-Methylindole-2-boronic acid, pinacol ester is a chemical compound that belongs to the class of boronic acid esters. It is derived from 1-methylindole and consists of a boronic acid functional group attached to a pinacol ester moiety. 1-Methylindole-2-boronic acid, pinacol ester is characterized by its unique structure and reactivity, making it a valuable tool in the field of organic chemistry for the construction of complex molecules.

596819-10-2

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596819-10-2 Usage

Uses

Used in Organic Synthesis:
1-Methylindole-2-boronic acid, pinacol ester is used as a reagent in organic synthesis for the formation of carbon-carbon bonds. Its application is particularly relevant in the Suzuki-Miyaura cross-coupling reaction, a widely used method for the formation of new carbon-carbon bonds between an aryl or vinyl halide and an organoboron compound.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 1-Methylindole-2-boronic acid, pinacol ester is used as a building block in the development of new drugs. Its unique structure and reactivity allow for the creation of complex molecular frameworks that can be tailored for specific therapeutic applications.
Used in Agrochemical Development:
Similarly, in the agrochemical industry, 1-Methylindole-2-boronic acid, pinacol ester is utilized as a building block for the synthesis of new agrochemicals. Its potential to form complex molecules makes it a valuable component in the development of novel pesticides and other agricultural chemicals designed to improve crop yield and protect against pests.

Check Digit Verification of cas no

The CAS Registry Mumber 596819-10-2 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 5,9,6,8,1 and 9 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 596819-10:
(8*5)+(7*9)+(6*6)+(5*8)+(4*1)+(3*9)+(2*1)+(1*0)=212
212 % 10 = 2
So 596819-10-2 is a valid CAS Registry Number.

596819-10-2 Well-known Company Product Price

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  • Aldrich

  • (704660)  1-Methyl-2-indoleboronicacidpinacolester  97%

  • 596819-10-2

  • 704660-1G

  • 1,074.06CNY

  • Detail
  • Aldrich

  • (704660)  1-Methyl-2-indoleboronicacidpinacolester  97%

  • 596819-10-2

  • 704660-5G

  • 3,280.68CNY

  • Detail

596819-10-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole

1.2 Other means of identification

Product number -
Other names 1-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:596819-10-2 SDS

596819-10-2Relevant articles and documents

Carbon-carbon bond activation by B(OMe)3/B2pin2-mediated fragmentation borylation

Chen, Quan,Jiang, Jiachen,Wang, Li,Wu, Aizhen,Yin, Youzhi,Zhang, Hua,Zhang, Ke,Zhao, Mengzhen,Zhong, Qi,Zou, Youliang

, p. 15104 - 15109 (2021/12/09)

Selective carbon-carbon bond activation is important in chemical industry and fundamental organic synthesis, but remains challenging. In this study, non-polar unstrained Csp2-Csp3 and Csp2-Csp2 bond activation was achieved by B(OMe)3/B2pin2-mediated fragmentation borylation. Various indole derivatives underwent C2-regioselective C-C bond activation to afford two C-B bonds under transition-metal-free conditions. Preliminary mechanistic investigations suggested that C-B bond formation and C-C bond cleavage probably occurred in a concerted process. This new reaction mode will stimulate the development of reactions based on inert C-C bond activation. This journal is

Benzoic Acid-Promoted C2-H Borylation of Indoles with Pinacolborane

Zou, Youliang,Zhang, Binfeng,Wang, Li,Zhang, Hua

supporting information, p. 2821 - 2825 (2021/04/13)

A benzoic acid-promoted C2-H borylation of indoles with pinacolborane to afford C2-borylated indoles is developed. Preliminary mechanistic studies indicate BH3-related borane species formed via the decomposition of pinacolborane to be the probable catalyst. This transformation provides a prompt route toward the synthesis of diverse C2-functionalized indoles.

Control Interlayer Stacking and Chemical Stability of Two-Dimensional Covalent Organic Frameworks via Steric Tuning

Wu, Xiaowei,Han, Xing,Liu, Yuhao,Liu, Yan,Cui, Yong

supporting information, p. 16124 - 16133 (2018/11/23)

Layer stacking and chemical stability are crucial for two-dimensional covalent organic frameworks (2D COFs), but are yet challenging to gain control. In this work, we demonstrate synthetic control of both the layer stacking and chemical stability of 2D COFs by managing interlayer steric hindrance via a multivariate (MTV) approach. By co-condensation of triamines with and without alkyl substituents (ethyl and isopropyl) and a di- or trialdehyde, a family of two-, three-, and four-component 2D COFs with AA, AB, or ABC stacking is prepared. The alkyl groups are periodically appended on the channel walls and their contents, which can be synthetically tuned by the MTV strategy, control the stacking model and chemical stability of 2D COFs by maximizing the total crystal stacking energy and protecting hydrolytically susceptible backbones through kinetic blocking. Specifically, the COFs with higher concentration of alkyl substituents adopt AB or ABC stacking, while lower amount of functionalities leads to the AA stacking. The COFs bearing high concentration of isopropyl groups represent the first identified COFs that can retain crystallinity and porosity in boiling 20 M NaOH solution. After postsynthetic metalation with an iridium complex, the 2,2′-bipyridyl-derived COFs can heterogeneously catalyze C-H borylation of arenes, whereas the COF with isopropyl groups exhibits much higher activity than the COFs with ethyl groups and nonsubstituents due to the increased porosity and chemical stability. This work underscores the opportunity in using steric hindrance to tune and control layer stacking, chemical stability and properties of 2D COFs.

Iridium/N-heterocyclic carbene-catalyzed C-H borylation of arenes by diisopropylaminoborane

Tobisu, Mamoru,Igarashi, Takuya,Chatani, Naoto

supporting information, p. 654 - 661 (2016/07/06)

Catalytic C-H borylation of arenes has been widely used in organic synthesis because it allows the introduction of a versatile boron functionality directly onto simple, unfunctionalized arenes. We report herein the use of diisopropylaminoborane as a boron source in C-H borylation of arenes. An iridium(I) complex with 1,3-dicyclohexylimidazol-2-ylidene is found to efficiently catalyze the borylation of arenes and heteroarenes. The resulting aminoborylated products can be converted to the corresponding boronic acid derivatives simply by treatment with suitable diols or diamines.

Fluorine-controlled C-H borylation of arenes catalyzed by a PSiN-pincer platinum complex

Takaya, Jun,Ito, Shisei,Nomoto, Hironori,Saito, Narumasa,Kirai, Naohiro,Iwasawa, Nobuharu

supporting information, p. 17662 - 17665 (2015/12/18)

An efficient, regioselective synthesis of fluorine-substituted arylboronic esters was achieved through fluorine-controlled C-H borylation of arenes with diboron catalyzed by a PSiN-platinum complex. The promising utility of the PSiN-platinum catalyst and its unique regioselectivity were demonstrated for the first time, which would complement the well-developed Ir-catalyzed C-H borylation.

BASE METAL CATALYZED BORYLATION OF ARENES AND AROMMATIC HETEROCYCLES

-

Page/Page column 34, (2015/06/25)

In one aspect, cobalt complexes are described herein. In some embodiments, such cobalt complexes employ bis(phosphine) or bis(imine) ligand and are operable as catalysts for borylation of arenes and aromatic heterocycles.

Cobalt-catalyzed C-H borylation

Obligacion, Jennifer V.,Semproni, Scott P.,Chirik, Paul J.

supporting information, p. 4133 - 4136 (2014/04/03)

A family of pincer-ligated cobalt complexes has been synthesized and are active for the catalytic C-H borylation of heterocycles and arenes. The cobalt catalysts operate with high activity and under mild conditions and do not require excess borane reagents. Up to 5000 turnovers for methyl furan-2-carboxylate have been observed at ambient temperature with 0.02 mol % catalyst loadings. A catalytic cycle that relies on a cobalt(I)-(III) redox couple is proposed.

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