913835-76-4

Usage

Uses

Used in Suzuki Reaction:
4-Chloro-2-formylbenzeneboronic acid 98 is used as a reagent in the Suzuki reaction, a widely employed cross-coupling reaction in organic chemistry. This reaction facilitates the formation of carbon-carbon bonds between an aryl or vinyl halide and an organoboron compound, leading to the synthesis of various organic compounds with potential applications in pharmaceuticals, agrochemicals, and materials science.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-chloro-2-formylbenzeneboronic acid 98 is used as a key intermediate in the synthesis of tetracyclic indole-based macrocycles. These macrocycles function as finger loop inhibitors of the HCV NS5b polymerase, an essential enzyme in the replication of the hepatitis C virus. By inhibiting this enzyme, the synthesis of viral RNA is disrupted, thus helping to combat the infection and treat the disease.
Overall, 4-chloro-2-formylbenzeneboronic acid 98 is a valuable compound with diverse applications in chemical synthesis and pharmaceutical development, making it an important tool for researchers and chemists in various fields.

InChI:InChI=1/C7H6BClO3/c9-6-1-2-7(8(11)12)5(3-6)4-10/h1-4,11-12H

Upstream product

• 174265-12-4 2-bromo-5-chlorobenzaldehyde 
• 1132669-91-0 C₁₃H₁₆BClO₃ 
• 209919-30-2 4-chloro-2-methylphenylboronic acid 
• 5419-55-6 Triisopropyl borate 

Downstream Products

• 1589546-22-4 C₂₉H₂₀ClO₂P 

Relevant academic research and scientific papers

Discovery of 3-aryl substituted benzoxaboroles as broad-spectrum inhibitors of serine- and metallo-β-lactamases

The production of β-lactamases represents the main cause of resistance to clinically important β-lactam antibiotics. Boron containing compounds have been demonstrated as promising broad-spectrum β-lactamase inhibitors to combat β-lactam resistance. Here we report a series of 3-aryl substituted benzoxaborole derivatives, which manifested broad-spectrum inhibition to representative serine-β-lactamases (SBLs) and metallo-β-lactamases (MBLs). The most potent inhibitor 9f displayed an IC50 value of 86 nM to KPC-2 SBL and micromolar inhibitory activity towards other tested enzymes. Cell-based assays further revealed that 9f was able to significantly reduce the MICs of meropenem in clinically isolated KPC-2-producing bacterial strains and it showed no apparent toxicity in HEK293T cells.

Design and enantioselective synthesis of 3-(α-acrylic acid) benzoxaboroles to combat carbapenemase resistance

Chiral 3-substituted benzoxaboroles were designed as carbapenemase inhibitors and efficiently synthesisedviaasymmetric Morita-Baylis-Hillman reaction. Some of the benzoxaboroles were potent inhibitors of clinically relevant carbapenemases and restored the activity of meropenem in bacteria harbouring these enzymes. Crystallographic analyses validate the proposed mechanism of binding to carbapenemases,i.e.in a manner relating to their antibiotic substrates. The results illustrate how combining a structure-based design approach with asymmetric catalysis can efficiently lead to potent β-lactamase inhibitors and provide a starting point to develop drugs combatting carbapenemases.

FLOW REACTION PROCESS FOR MANUFACTURE OF BORON-CONTAINING AGROCHEMICALS

The present invention relates to methods of preparing benzoxaboroles. Benzoxaborole compounds have shown promise as antimicrobial agents, especially against fungal pathogens. The invention also relates to compositions of acyclic alkoxy boronic acid esters as intermediates, and continuous flow processes of mixing the intermediates with organomagnesium, magnesium, or organolithium reagents to form the desired benzoxaboroles.

Synthesis of naphthalene ring derivatives and Benzoheterocycles the method of the compound

The invention discloses a method for synthesizing naphthalene derivative and benzo-heterocycle compounds. The method is realized by promoting a reaction similar to Mortia-Baylis-Hillman between aryl aldehyde having alpha, beta-unsaturated ester on ortho-position and ketone compounds under the catalysis action of tertiary amine and tertiary phosphine organic small molecular catalysts, so as to remove a molecule of H2O, so that the naphthalene derivative or benzo-heterocycle compounds are generated. The method disclosed by the invention is simple in operation step, cheap and easily available in adopted catalysts and harmless to environment, and a series of naphthalene derivative and benzo-heterocycle compounds are synthesized with relatively high yield.