408492-29-5

Basic information

• Product Name: 3-Chloro-5-methoxycarbonyl-phenyl-boronic acid pinacol ester
• Synonyms: 3-Chloro-5-methoxycarbonyl-phenyl-boronic acid pinacol ester;Methyl 3-chloro-5-(hydroxy((3-hydroxy-2,3-dimethylbutan-2-yl)oxy)boryl)benzoate;3-Chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester
• CAS NO: 408492-29-5
• Molecular Formula: C₁₄H₁₈BClO₄
• Molecular Weight: 314.5696
• Mol File: 408492-29-5.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Chloro-5-methoxycarbonyl-phenyl-boronic acid pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Chloro-5-methoxycarbonyl-phenyl-boronic acid pinacol ester(408492-29-5)
• EPA Substance Registry System: 3-Chloro-5-methoxycarbonyl-phenyl-boronic acid pinacol ester(408492-29-5)

Safety Data

• Hazardous Substances Data: 408492-29-5(Hazardous Substances Data)

Usage

Description

3-Chloro-5-methoxycarbonyl-phenyl-boronic acid pinacol ester is an organic compound that features a boronic acid group and a pinacol ester group. It is recognized for its utility in organic synthesis, particularly within the realm of Suzuki-Miyaura cross-coupling reactions. 3-Chloro-5-methoxycarbonyl-phenyl-boronic acid pinacol ester serves as a valuable building block in the pharmaceutical and agrochemical sectors, as well as in the synthesis of various organic materials. Its potential extends to the development of innovative drugs and materials, making it a significant player in the advancement of chemical research and applications.

Uses

Used in Pharmaceutical Industry:
3-Chloro-5-methoxycarbonyl-phenyl-boronic acid pinacol ester is utilized as a key intermediate for the synthesis of complex organic molecules, particularly in the development of new drugs. Its ability to form new carbon-carbon bonds through Suzuki-Miyaura cross-coupling reactions facilitates the creation of diverse molecular structures, which is crucial for the discovery of novel pharmaceutical agents.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Chloro-5-methoxycarbonyl-phenyl-boronic acid pinacol ester is employed as a reagent for the synthesis of various agrochemicals. Its role in forming new carbon-carbon bonds is vital for the development of effective and innovative agrochemical products, contributing to enhanced crop protection and yield.
Used in Organic Material Synthesis:
3-Chloro-5-methoxycarbonyl-phenyl-boronic acid pinacol ester is used as a building block in the synthesis of organic materials. Its involvement in creating new carbon-carbon bonds is essential for the development of advanced materials with unique properties, such as those used in electronics, plastics, and other high-performance applications.
Used in Drug Development:
3-Chloro-5-methoxycarbonyl-phenyl-boronic acid pinacol ester is also used as a precursor in the development of new drugs. Its potential applications in medicinal chemistry are vast, as it can be incorporated into drug candidates to enhance their pharmacological properties, such as potency, selectivity, and bioavailability.

Upstream product

• 2905-65-9 methyl 3-chlorobenzoate 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 73183-34-3 bis(pinacol)diborane 

Downstream Products

• 957120-26-2 [3-chloro-5-(methoxycarbonyl)phenyl]boronic acid 
• 1033945-11-7 C₁₅H₁₀ClNO₂ 
• 879542-53-7 3-chloro-5-pyridin-2-yl-benzoic acid methyl ester 
• 98406-04-3 methyl 3-chloro-5-hydroxybenzoate 

Relevant articles and documents

Two Ligands Transfer from Ag to Pd: En Route to (SIPr)Pd(CF2H)(X) and Its Application in One-Pot C-H Borylation/Difluoromethylation

A process for the concurrent transfer of both the NHC ligand and the difluoromethyl group from [(SIPr)Ag(CF2H)] to PdX2 (X = Cl, OAc, and OPiv) for the preparation of [(SIPr)Pd(CF2H)X] complexes is described. These complexes were air-stable and easily underwent transmetalation with aryl pinacol boronate/reductive elimination to generate ArCF2H in high yields. Based on this discovery, the first one-pot C-H borylation and difluoromethylation process for the preparation of difluoromethylated (hetero)arenes was developed.

Practical one-pot C-H activation/borylation/oxidation: Preparation of 3-bromo-5-methylphenol on a multigram scale

A practical one-pot C-H activation/borylation/oxidation sequence for the generation of 3,5-disubstituted phenols is presented. Specifically, 3-bromo-5-methylphenol is prepared from 3-bromotoluene, without isolation of intermediates, on a multigram scale, and in high yield. The process proceeds under mild conditions and can be completed within one day. Georg Thieme Verlag Stuttgart - New York.

Iridium-catalyzed C-H borylation of arenes and heteroarenes: 1-chloro-3-iodo-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene and 2-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)indole: (2-(3-chloro-5-iodophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane) (2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole)

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