1073354-10-5

Basic information

• Product Name: 2-(TERT-BUTYLCARBONYLAMINO)PHENYLBORONIC ACID, PINACOL ESTER
• Synonyms: 2-(TERT-BUTYLCARBONYLAMINO)PHENYLBORONIC ACID, PINACOL ESTER;2,2-DIMETHYL-N-[2-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL]PROPIONAMIDE;2-(tert-Butylcarbonylamino)phenylboronic acid,pinacol
• CAS NO: 1073354-10-5
• Molecular Formula: C₁₇H₂₆BNO₃
• Molecular Weight: 303.2
• Mol File: 1073354-10-5.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(TERT-BUTYLCARBONYLAMINO)PHENYLBORONIC ACID, PINACOL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(TERT-BUTYLCARBONYLAMINO)PHENYLBORONIC ACID, PINACOL ESTER(1073354-10-5)
• EPA Substance Registry System: 2-(TERT-BUTYLCARBONYLAMINO)PHENYLBORONIC ACID, PINACOL ESTER(1073354-10-5)

Safety Data

• Hazardous Substances Data: 1073354-10-5(Hazardous Substances Data)

Usage

Description

2-(Tert-Butylcarbonylamino)phenylboronic acid, pinacol ester is a versatile chemical compound that is widely used in organic synthesis and medicinal chemistry. It is a pinacol ester of 2-(tert-butylcarbonylamino)phenylboronic acid, which is a derivative of boronic acid. 2-(Tert-Butylcarbonylamino)phenylboronic acid, pinacol ester is known for its ability to selectively inhibit proteasome activity, making it a promising candidate for the development of new pharmaceuticals. Additionally, it has been investigated for its potential use in materials science, particularly in the development of organic electronic materials.

Uses

Used in Organic Synthesis:
2-(Tert-Butylcarbonylamino)phenylboronic acid, pinacol ester is used as a reagent in cross-coupling reactions, such as Suzuki-Miyaura coupling, for the formation of carbon-carbon bonds. Its ability to participate in these reactions makes it a valuable tool in the synthesis of complex organic molecules.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 2-(Tert-Butylcarbonylamino)phenylboronic acid, pinacol ester is used as a potential candidate for developing new pharmaceuticals. Its selective inhibition of proteasome activity suggests its potential use in the treatment of various diseases, including cancer.
Used in Materials Science:
2-(Tert-Butylcarbonylamino)phenylboronic acid, pinacol ester is also used in materials science, particularly in the development of organic electronic materials. Its unique properties make it a promising candidate for applications in organic electronics, such as organic light-emitting diodes (OLEDs) and organic photovoltaics (OPVs).
Used in Pharmaceutical Development:
In the pharmaceutical industry, 2-(Tert-Butylcarbonylamino)phenylboronic acid, pinacol ester is used as a key intermediate in the synthesis of various drug molecules. Its ability to selectively inhibit proteasome activity makes it a valuable compound for the development of targeted therapies against specific diseases.
Overall, 2-(Tert-Butylcarbonylamino)phenylboronic acid, pinacol ester is a versatile and valuable chemical compound with a wide range of applications in various fields, including organic synthesis, medicinal chemistry, materials science, and pharmaceutical development. Its unique properties and potential uses make it an important compound for ongoing research and development efforts.

Upstream product

• 6625-74-7 N-pivaloylaniline 
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Downstream Products

• 797047-16-6 2,2-dimethyl-N-(2-pyrimidin-2-yl-phenyl)-propionamide 
• 146141-10-8 N-[2-(3-fluoropyridin-2-yl)phenyl]-2,2-dimethylpropionamide 
• 1615683-42-5 2-(5-(4-amino-3-(3-fluoropyridin-2-yl)-5-nitrophenyl)-pyrimidin-2-yl)propan-2-ol 
• 1615683-35-6 C₁₆H₁₁FN₄O₃ 
• 1615683-31-2 C₂₀H₁₉FN₆O₃ 
• 797047-20-2 2-Nitro-6-pyrimidin-2-yl-4-(4,4,5,5-tetramethyl-[1,3,2] dioxaborolan-2-yl)-phenylamine 
• 1052686-59-5 2-(3-fluoropyridin-2-yl)-6-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 
• 797047-19-9 4-bromo-2-nitro-6-(pyrimidin-2-yl)benzenamine 
• 1052686-58-4 4-bromo-2-(3-fluoropyridin-2-yl)-6-nitrophenylamine 

Relevant articles and documents

Acyl-Directed ortho-Borylation of Anilines and C7 Borylation of Indoles using just BBr3

Indoles are privileged heterocycles found in many biologically active pharmaceuticals and natural products. However, the selective functionalization of the benzenoid moiety in indoles in preference to the more reactive pyrrolic unit is a significant challenge. Herein we report that N-acyl directing groups enable the C7-selective C?H borylation of indoles using just BBr3. This transformation shows some functional-group tolerance and notably proceeds with C6 substituted indoles. The directing group can be readily removed in situ and the products isolated as the pinacol boronate esters. Acyl-directed electrophilic borylation can be extended to carbazoles and anilines with excellent ortho selectivity. 4-amino-indoles are amenable to this process, with acyl group installation and directed electrophilic C?H borylation enabling selective formation of C5-BPin-indoles.

Preparation method of indole type or aniline type borate

The invention discloses a preparation method of indole type or aniline type borate, which comprises the following step: reacting an indole type raw material or aniline type raw material with boron trihalide in an organic solvent under the protection of in

NiCl2(PMe3)2-catalyzed borylation of aryl chlorides

The cross-coupling of aryl chlorides and bis(pinacolato)diboron was achieved using NiCl2(PMe3)2 catalyst in the presence of metal 2,2,2-trifluoroethoxide. The catalyst smoothly provided the desired products regardless of a variety of functional groups and substituted positions.