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

General Description

3-Chloro-5-methoxycarbonyl-phenyl-boronic acid pinacol ester is an organic compound that consists of a boronic acid group and a pinacol ester group. It is a useful reagent in organic synthesis, particularly in Suzuki-Miyaura cross-coupling reactions. 3-Chloro-5-methoxycarbonyl-phenyl-boronic acid pinacol ester is often used to introduce the 3-chloro-5-methoxycarbonyl-phenyl-boronic acid pinacol ester group into organic molecules, allowing for the formation of new carbon-carbon bonds. It is an important building block in the pharmaceutical and agrochemical industries, as well as in the synthesis of organic materials. Additionally, this compound has potential applications in the development of new drugs and materials.

Upstream product

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

Downstream Products

• 1033945-11-7 C₁₅H₁₀ClNO₂ 
• 957120-26-2 [3-chloro-5-(methoxycarbonyl)phenyl]boronic acid 
• 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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