40138-16-7

Basic information

• Product Name: 2-Formylbenzeneboronic acid
• Synonyms: RARECHEM AH PB 0192;BENZALDEHYDE-2-BORONIC ACID;AKOS BRN-0109;2-BORONOBENZALDEHYDE;2-FORMYLPHENYLBORONIC ACID;2-FORMYLBENZENEBORONIC ACID;2-(DIHYDROXYBORYL)BENZALDEHYDE;2-Boronobenzaldehyde~2-Formylphenylboronic acid
• CAS NO: 40138-16-7
• Molecular Formula: C₇H₇BO₃
• Molecular Weight: 149.94
• EINECS: -0
• Product Categories: Aldehydes;blocks;BoronicAcids;Boronic Acid series;Substituted Boronic Acids;Boronic Acids & Esters;Phenyls & Phenyl-Het;Boronic acids;Boronic Acid;Aldehyde;Aryl;Organoborons;B (Classes of Boron Compounds);Boronic Acids & Esters;Phenyls & Phenyl-Het
• Mol File: 40138-16-7.mol
• Article Data: 18

Chemical Properties

• Melting Point: 115-120 °C(lit.)
• Boiling Point: 355.7 °C at 760 mmHg
• Flash Point: 169 °C
• Appearance: Light yellow to light orange-pink/Crystalline Powder or Needles and Chunks
• Density: 1.24 g/cm³
• Vapor Pressure: 1.12E-05mmHg at 25°C
• Refractive Index: 1.547
• Storage Temp.: 0-6°C
• Solubility: Soluble in methanol.
• PKA: 8.18±0.53(Predicted)
• Sensitive: Air Sensitive
• BRN: 3030776
• CAS DataBase Reference: 2-Formylbenzeneboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Formylbenzeneboronic acid(40138-16-7)
• EPA Substance Registry System: 2-Formylbenzeneboronic acid(40138-16-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 40138-16-7(Hazardous Substances Data)

Usage

Chemical Properties

light yellow to light orange-pink crystalline

Uses

Different sources of media describe the Uses of 40138-16-7 differently. You can refer to the following data:
1. suzuki reaction
2. 2-Formylbenzeneboronic acid is used as an organic chemical synthesis intermediate.

InChI:InChI=1/C7H7BO3/c9-5-6-3-1-2-4-7(6)8(10)11/h1-5,10-11H

Upstream product

• 34824-58-3 2-(2-bromophenyl)-1,3-dioxolan 
• 121-43-7 Trimethyl borate 
• 112627-02-8 (2-Br₂CHC₆H₄)B(OH)2 
• 35849-09-3 o-bromobenzaldehyde dimethyl acetal 
• 17604-70-5 2-(((methoxy)imino)methyl)phenylboronic acid 
• 6630-33-7 ortho-bromobenzaldehyde 
• 1229227-01-3 C₁₈H₁₂B₃Br₃O₃ 
• 68-12-2 N,N-dimethyl-formamide 
• 5419-55-6 Triisopropyl borate 
• 7294-50-0 tri-o-tolylboroxine 
• 932-31-0 ortho-tolylmagnesium bromide 
• 35364-86-4 2-chlorobenzaldehyde diethyl acetal 
• 16419-60-6 2-Methylphenylboronic acid 

Downstream Products

• 19203-45-3 Boronophthalidyl-essigsaeure 
• 176526-00-4 2-(pyridin-4-yl)benzaldehyde 
• 898821-54-0 2-(9-phenanthryl)benzenecarboxaldehyde 
• 205871-49-4 2'-formylbiphenyl-4-carboxylic acid 
• 380151-85-9 2-(2'-formylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 476171-98-9 2-(5-methoxy-1-methyl-6-oxo-1,6-dihydropyridazin-4-yl)benzaldehyde 
• 476172-02-8 2-(2-benzyl-5-methoxy-3-oxo-2,3-dihydropyridazin-4-yl)benzaldehyde 
• 476171-97-8 2-(1-benzyl-5-methoxy-6-oxo-1,6-dihydropyridazin-4-yl)benzaldehyde 
• 1210-05-5 Biphenyl-2,2'-dicarbaldehyde 

Relevant articles and documents

Tuning the exchange dynamics of boronic acid hydrazones and oximes with pH and redox control

Dynamic bonds continually form and dissociate at equilibrium. Carbonyl compounds with proximal boronic acids, including 2-formylphenylboronic acid (2-FPBA), have been reported to form highly dynamic covalent hydrazone and oxime bonds in physiological conditions, but strategies to tune the dynamics have not yet been reported. Here, we characterize the dynamics of 2-FPBA-derived hydrazones and oximes and account for both the rapid rate of formation (～102-103M?1s?1) and the relatively fast rate of hydrolysis (～10?4s?1) at physiological pH. We further show that these substrates undergo exchange with α-nucleophiles, which can be reversibly paused and restarted with pH control. Finally, we show that oxidation of the arylboronic acid effectively abolishes the rapid dynamics, which slows the forward reaction by more than 30?000 times and increases the hydrolytic half-life from 50 minutes to 6 months at physiological pH. These results set the stage to explore these linkages in dynamic combinatorial libraries, reversible bioconjugation, and self-healing materials.

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.