139962-95-1

Usage

Chemical Properties

white to light yellow powder

Uses

suzuki reaction

InChI:InChI=1/C8H9BO4/c1-13-7-2-3-8(9(11)12)6(4-7)5-10/h2-5,11-12H,1H3

Upstream product

• 98015-07-7 2-Bromo-5-methoxybenzaldehyde ethylene glycol acetal 
• 5419-55-6 Triisopropyl borate 
• 1132669-90-9 5-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde 
• 121-43-7 Trimethyl borate 
• 181780-66-5 1-bromo-2-(dimethoxymethyl)-4-methoxybenzene 
• 591-31-1 3-methoxy-benzaldehyde 
• 19614-12-1 2-bromo-5-methoxybenzyl bromide 
• 27060-75-9 4-bromo-3-methylanisole 
• 1186304-21-1 2-(2-bromo-5-methoxyphenyl)-1,3-dioxane 
• 7507-86-0 2-bromo-5-methoxy-benzaldehyde 

Downstream Products

• 354529-43-4 3-(2-Formyl-4-methoxyphenyl)dibenzo[b,d]thiophene 
• 485824-20-2 1-(2-formyl-4-methoxyphenyl)dibenzothiophene 
• 671780-73-7 5-methoxy-2-(1,4-dimethoxynaphthalen-2-yl)benzaldehyde 
• 1132669-90-9 5-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde 
• 681215-17-8 7-(2-formyl-4-methoxyphenyl)-5,6-dihydro-4H-benz[de]anthracene 
• 830328-51-3 C₄₀H₂₈N₂O₄ 
• 842167-37-7 7-(2-formyl-4-methoxyphenyl)benzo[b]thiophene 
• 958002-18-1 1H-indole-6-carboxylic acid, 3-cyclohexyl-2-(2-formyl-4-methoxyphenyl)-, 1,1-dimethylethyl ester 
• 760206-01-7 2-[(7bR,11aS)-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indol-6-yl]-5-methoxybenzaldehyde, Trifluoroacetic Acid Salt 
• 762263-92-3 (2-(hydroxymethyl)-4-methoxyphenyl)boronic acid 
• 960361-38-0 (HO)2BC₆H₃(OCH₃)CHNNHCOC₅H₄N 
• 958002-14-7 6H-Isoindolo[2,1-a]indole-3-carboxamide, 11-cyclohexyl-N-[(dimethylamino)sulfonyl]-6-ethoxy-8-methoxy- 
• 1246404-40-9 C₁₇H₁₅BO₅ 
• 1266162-03-1 6-(2-formyl-4-methoxyphenyl)-4-(methylthio)-2,3'-bipyridine-5-carbonitrile 

Relevant academic research and scientific papers

Sustainable Passerini-tetrazole three component reaction (PT-3CR): selective synthesis of oxaborol-tetrazoles

A sustainable catalyst- and solvent-free Passerini-tetrazole three component reaction (PT-3CR) has been developed for the selective synthesis of benzoxaborol-tetrazoles for the first time. The synthetic potential of oxaboroles was demonstrated towards various functionalized tetrazoles, which are otherwise difficult to achieve through conventional PT-3CR from aromatic aldehydes/ketones. The reaction features high practicality, broad substrate scope and excellent yields (80-98%). Preliminary results of the asymmetric PT-3CR are also shown for the synthesis of chiral benzoxaboroles.

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.

The First Kilogram Synthesis of Beclabuvir, an HCV NS5B Polymerase Inhibitor

The process development and kilogram-scale synthesis of beclabuvir (BMS-791325, 1) is described. The convergent synthesis features the use of asymmetric catalysis to generate a chiral cyclopropane fragment and coupling with an indole fragment via an alkyl

Highly fluorescent, π-extended indenopyrido[2,1-a]isoindolone derivatives prepared by a palladium-catalysed cascade reaction

A new family of heterocyclic pentacyclic compounds have been prepared by a cascade reaction involving 2,5-dihalopyridines and (2-formylphenyl)boronic acids. Most of the compounds exhibit high quantum yields of fluorescence in dichloromethane. In some cases, small changes in the substitution pattern caused fluorescence quenching. To rationalize this effect, a detailed photophysical study combined with electrochemical and computational studies was performed on four representative derivatives. It appears that the fluorescence quenching is caused by a thermally activated non-radiative deactivation process that can be prevented in a rigid matrix such as ethanol at 77 K or a PMMA polymer.

Internal Lewis acid assisted benzoic acid catalysis

Internal Lewis acid assisted benzoic acid derivatives are introduced as new low-molecular-weight single-hydrogen-bond donor catalysts for the activation of nitroalkenes. Selected 2-borylbenzoic acid derivatives gave good yields of products in the addition of indoles to nitroalkenes. Control experiments suggest that both the internal Lewis acid coordination and the carboxylic acid functionalities are critical to the optimal performance of these catalysts. Georg Thieme Verlag Stuttgart New York.

Total synthesis of plagiochin D by an intramolecular SNAr reaction

The total synthesis of plagiochin D, a macrocyclic bis(bibenzyl) compound isolated from the liverwort plagiochila acanthophylla, has been accomplished. Closure of the key 16-membered ring, which contained biphenyl ether and biaryl units, was achieved in good yield by an intramolecular SNAr reaction. The Suzuki and Wittig protocols proved to be powerful tools for the construction of a linear precursor that was crucial for ring cyclization. Copyright

Syntheses of macrocyclic bis(bibenzyl) compounds derived from perrottetin e

Macrocyclic bis(bibenzyl) compounds are natural products from liverworts and are of growing interest due to recent reports on new isolated compounds and on their remarkable biological activities. We report here on a flexible and general approach to the to

A synthesis-driven structure revision of 'plagiochin E', a highly bioactive bisbibenzyl

Recently, a bisbibenzyl named plagiochin E showing remarkable antifungal and antitumor activities was isolated from Marchantia polymorpha, a liverwort. The total synthesis of the proposed structure for plagiochin E and of two structurally and biosynthetic

Synthesis of a highly soluble superstructured phenanthroline strapped porphyrin

A highly soluble phenanthroline strapped porphyrin is prepared on multigram scale by appropriate functionalization with C12 chains a posteriori to the efficient cyclization of the tetrapyrrolic macrocycle. A highly soluble phenanthroline strapp