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

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

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

Downstream Products

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

Recyclable silica-supported iridium bipyridine catalyst for aromatic C-H borylation

A mesoporous silica (SBA-15)-supported bipyridine iridium complex is prepared by grafting of bipyridine onto the silica support, followed by complexation of an iridium(I) precursor in the presence of HBpin and cyclooctene. Structural analyses by X-ray powder diffraction, nitrogen physisorption, FT-IR, and solid-state NMR spectroscopy demonstrate that the 3-dimensional, hexagonal pore structure of SBA-15 is maintained after the immobilization. In particular, as a heterogeneous catalyst, this silica-supported iridium complex shows moderate to good catalytic activity in the aromatic C-H borylation of a variety of substrates. More importantly, the heterogeneous catalyst is recovered easily and reused repeatedly by simple washing without chemical treatment and exhibits good recycling performance with a modest decrease in the catalytic rate, showing good potential for increasing the overall turnover number of this synthetically useful catalyst.

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.

Practical synthesis of pinacolborane for one-pot synthesis of unsymmetrical biaryls via aromatic C-H borylation-cross-coupling sequence

A method for practical preparation of pinacolborane from borane-diethylaniline and pinacol was newly developed. Aromatic C-H borylation of arenes with pinacolborane or bis(pinacolato)diboron catalyzed by 1/2[Ir(OMe)(COD)]2-(4,4′-di-tert-butyl-2,2′-bipyridine) at 25 °C in hexane to give arylboronic esters was directly followed by cross-coupling with aromatic bromides at 60 °C in the presence of PdCl2(dppf) (3.0 mol %) and K3PO4 in DMF. This one-pot, two-step procedure provided a variety of unsymmetrical biaryls in high yields.

Process for the synthesis of phenols from arenes

A process to synthesize substituted phenols such as those of the general formula RR′R″Ar(OH) wherein R, R′, and R″ are each independently hydrogen or any group which does not interfere in the process for synthesizing the substituted phenol including, but not limited to, halo, alkyl, alkoxy, carboxylic ester, amine, amide; and Ar is any variety of aryl or hetroaryl by means of oxidation of substituted arylboronic esters is described. In particular, a metal-catalyzed C—H activation/borylation reaction is described, which when followed by direct oxidation in a single or separate reaction vessel affords phenols without the need for any intermediate manipulations. More particularly, a process wherein Ir-catalyzed borylation of arenes using pinacolborane (HBPin) followed by oxidation of the intermediate arylboronic ester by OXONE is described.

Room temperature borylation of arenes and heteroarenes using stoichiometric amounts of pinacolborane catalyzed by iridium complexes in an inert solvent

Aromatic C-H borylation of arenes and heteroarenes using stoichiometric amounts of pinacolborane was catalyzed by an iridium complex generated from 1/2 [Ir(OMe)(COD)]2 and 4,4′-di-tert-butyl-2,2′-bipyridine at room temperature in hexane and aff

C-H activation/borylation/oxidation: A one-pot unified route to meta-substituted phenols bearing ortho-/para-directing groups

An efficient one-pot C-H activation/borylation/oxidation protocol for the preparation of phenols is described. This method is particularly attractive for the generation of meta-substituted phenols bearing ortho-/para-directing groups, as such substrates are difficult to access by other phenol syntheses. Copyright

A stoichiometric aromatic C-H borylation catalyzed by iridium(I)/2,2′-bipyridine complexes at room temperature

Room-temperature C-H borylation using a stoichiometric amount of arenes and bis(pinacolato)diboron (pin2B2) is efficiently catalyzed by iridium(I) complexes generated from [{Ir(OMe)(cod)}2] (cod=1,5-cyclooctadiene) and 4,4′-di-tertbutyl-2,2′-bipyridine (dtbpy) in hexane, and provides the corresponding arylboronates in excellent yields [Eq. (1)].