174671-49-9

Upstream product

• 5419-55-6 Triisopropyl borate 
• 59142-47-1 (2-bromophenyl)phenylmethanol 
• 1171115-60-8 C₁₅H₁₅BrO₂ 
• 100-58-3 phenylmagnesium bromide 
• 6630-33-7 ortho-bromobenzaldehyde 
• 73183-34-3 bis(pinacol)diborane 

Relevant academic research and scientific papers

Practical synthesis and applications of benzoboroxoles

A convenient one-pot synthesis of benzoboroxoles has been developed via the reaction of o-bromobenzyl alcohols with NaH, nBuLi, and B(OiPr)3 followed by acidic hydrolysis. Applications of these benzoboroxoles have been demonstrated in Pd-catalyzed cross-coupling reactions and the protocol has been extended for the synthesis of a chiral benzoboroxole. Exceptionally short synthesis of a potent antifungal agent AN2690 and several of its analogs has also been realized.

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.

Benzoborate synthesis method

The present invention relates to a benzoborate synthesis method, which comprises that under the protection of nitrogen, o-halo aryl alcohol and bis(pinacolato)diboron are adopted as reaction substrates, and a Miyaura coupling series connection reaction is performed for 12-16 h at a temperature of 80-110 DEG C under catalysis of palladium to perform one-step synthesis of a multi-substituted or multi-functionalized benzoborate compound, wherein the palladium catalyst is bistriphenylphosphinepalladium bichloride, a mixture comprising palladium acetate and 1,1'-bis(diphenylphosphine)ferrocene according to a molar ratio of 1:2, tetrakistriphenylphosphine palladium or 1,1'-bis(diphenylphosphine)ferrocene palladium dichloride, a molar ratio of the reaction substrate o-halo aryl alcohol to the reaction substrate bis(pinacolato)diboron to the palladium catalyst to the alkali is 1:1.2-1.5:0.05-0.1:3-6. The synthesis method of the present invention has characteristics of simple process and high product yield.

One-pot synthesis of benzoxaborole derivatives from the palladium-catalyzed cross-coupling reaction of alkoxydiboron with unprotected o-bromobenzylalcohols

Under very mild conditions, functionalized benzoxaborole derivatives were prepared in good to excellent yields via a palladium-catalyzed Miyaura borylation reaction of readily available unprotected o-bromobenzylalcohols, and bis(pinacolato)diboron (B2pin2) without the assistance of an acid. Blue-light-emitting materials based on spiro benzoxaborole building blocks have been obtained with potential applications in organic electronics and biomedicine.

Influence of the substituents on the structure and properties of benzoxaboroles

Benzoxaboroles possessing aryl substituents in the oxaborole ring were synthesized, and their structures were detennined by single-crystal X-ray diffraction. Structures in the solid state are centrosymmetric dimers with two intermolecular hydrogen bonds. These compounds were investigated using a combination of the spectroscopic and the computational approach, comparing their properties with the unsubstituted compound. Investigated compounds were characterized by 1H, 13C, and 11B NMR spectroscopy in solution. Assignment of 1H and 13C signals was made on the basis of HSQC and HMBC spectra. The molecular structure of 1,3dihydro-1-hydroxy-3-phenyl-2,1-benzoxaborole was calculated by the density functional (B3LYP) method with the extended 6-311++G(d,p) basis set. The calculated geometrical parameters were compared with experimental X-ray data, and the differences between experimental and calculated values were found to be of the order of experiment standard deviation, confirming a good description by this level of theory. The harmonic frequencies, potential energy distribution (PED), and IR intensities of this compound and its deuterated analogue were calculated with the B3LYP method. The assignment of the experimental spectra was made on the basis of the calculated PED. The consequence of dimer formation is the splitting of the vibrational modes into symmetric and antisymmetric vibrations. The structure modification resulting from the hydrogen bonded dimers formation is presented.

Oxaboroles and salts thereof, and their use as biocides

A method for the protection of a medium by susceptible to microbial attack by the treatment of the medium with an oxaborale or a salt of an oxaborale.