98437-23-1 | Benzo(b)thiophene-2-boronic acid

Packsize	Purity	Availability	Price	Discounted Price
250mg	97%	in stock	$8.00	$5.00
1g	97%	in stock	$13.00	$9.00
5g	97%	in stock	$19.00	$14.00
10g	97%	in stock	$25.00	$18.00
25g	97%	in stock	$59.00	$42.00
100g	97%	in stock	$213.00	$150.00

Description

• Catalog Number: AB61252
• Chemical Name: Benzo(b)thiophene-2-boronic acid
• CAS Number: 98437-23-1
• Molecular Formula: C8H7BO2S
• Molecular Weight: 178.016
• MDL Number: MFCD01075674
• SMILES: OB(c1cc2c(s1)cccc2)O

Computed Properties

• Complexity: 165
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 12
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 2
• Rotatable Bond Count: 1

Upstream Synthesis Route

Benzo[b]thiophen-2-ylboronic acid is a versatile chemical compound commonly used in chemical synthesis processes. Due to its boronic acid functional group, this compound serves as a valuable building block in organic chemistry. In the realm of chemical synthesis, Benzo[b]thiophen-2-ylboronic acid acts as a key reagent in Suzuki-Miyaura cross-coupling reactions. This reaction involves the coupling of an aryl or vinyl boronic acid with an organic halide or triflate, catalyzed by a palladium(0) complex, to form a new carbon-carbon bond. By participating in this important reaction, Benzo[b]thiophen-2-ylboronic acid enables the creation of complex organic molecules with precise control over the connectivity and stereochemistry of the newly formed bonds. In addition to its role in cross-coupling reactions, Benzo[b]thiophen-2-ylboronic acid also finds applications in the synthesis of pharmaceuticals, agrochemicals, and materials with tailored properties. Its ability to facilitate the formation of carbon-carbon bonds makes it a valuable tool for chemists working in various fields of research and industry.

Literature

• Permeation through the cell membrane of a boron-based β-lactamase inhibitor.

  PloS one 20110101

• Structural bases for stability-function tradeoffs in antibiotic resistance.

  Journal of molecular biology 20100212

• Synthesis and evaluation of 3-(dihydroxyboryl)benzoic acids as D,D-carboxypeptidase R39 inhibitors.

  Journal of medicinal chemistry 20091008

• Discovery of boronic acids as novel and potent inhibitors of fatty acid amide hydrolase.

  Journal of medicinal chemistry 20081127

• Optimizing cell permeation of an antibiotic resistance inhibitor for improved efficacy.

  Journal of medicinal chemistry 20071115

• A versatile synthesis of 17-heteroaryl androstenes via palladium-mediated Suzuki cross-coupling with heteroaryl boronic acids.

  Steroids 20060701

• Activity of mecillinam against AmpC beta-lactamase-producing Escherichia coli.

  The Journal of antimicrobial chemotherapy 20060701

• Disc methods for detecting AmpC {beta}-lactamase-producing clinical isolates of Escherichia coli and Klebsiella pneumoniae.

  The Journal of antimicrobial chemotherapy 20050901

• Characterization of beta-lactamases responsible for resistance to extended-spectrum cephalosporins in Escherichia coli and Salmonella enterica strains from food-producing animals in the United Kingdom.

  Microbial drug resistance (Larchmont, N.Y.) 20040101

• Effect of detergent on 'promiscuous' inhibitors.

  Journal of medicinal chemistry 20030731

• Kinase inhibitors: not just for kinases anymore.

  Journal of medicinal chemistry 20030410

• Structure-based approach for binding site identification on AmpC beta-lactamase.

  Journal of medicinal chemistry 20020718

• A common mechanism underlying promiscuous inhibitors from virtual and high-throughput screening.

  Journal of medicinal chemistry 20020411