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

Description

2-Formylbenzeneboronic acid is an organic compound that serves as a versatile intermediate in chemical synthesis. It is characterized by its light yellow to light orange-pink crystalline appearance and is commonly utilized in various chemical reactions due to its unique chemical properties.

Uses

Used in Organic Synthesis:
2-Formylbenzeneboronic acid is used as an organic chemical synthesis intermediate for its ability to participate in a wide range of chemical reactions, including the Suzuki reaction. This reaction is a cross-coupling reaction between an organoboron compound and an organic halide or triflate, which is widely used in the synthesis of complex organic molecules, particularly in the pharmaceutical and materials science industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Formylbenzeneboronic acid is used as a key intermediate in the synthesis of various drugs and drug candidates. Its reactivity and stability make it a valuable component in the development of new medications with potential therapeutic applications.
Used in Materials Science:
2-Formylbenzeneboronic acid is also employed in the field of materials science, where it is used to synthesize novel materials with specific properties. These materials can be utilized in various applications, such as in the development of advanced electronic devices, sensors, and other high-tech applications.
Used in Research and Development:
Due to its unique chemical properties and reactivity, 2-Formylbenzeneboronic acid is often used in research and development laboratories to explore new chemical reactions and develop innovative synthetic methods. This contributes to the advancement of chemical science and the discovery of new compounds with potential applications in various industries.

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 
• 5419-55-6 Triisopropyl borate 
• 6630-33-7 ortho-bromobenzaldehyde 
• 1229227-01-3 C₁₈H₁₂B₃Br₃O₃ 
• 68-12-2 N,N-dimethyl-formamide 
• 35849-09-3 o-bromobenzaldehyde dimethyl acetal 
• 17604-70-5 2-(((methoxy)imino)methyl)phenylboronic acid 
• 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 
• 380151-85-9 2-(2'-formylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 99902-07-5 2-(2-thienyl)benzaldehyde 
• 99902-03-1 2-(thien-3-yl)benzaldehyde 
• 176690-44-1 2-(pyridin-3-yl)benzaldehyde 
• 280584-50-1 (E)-2-[2-(2-Phenylethenyl)cyclopentenyl]benzaldehyde 
• 280584-58-9 (E)-2-[2-(2-Methoxycarbonylethenyl)cyclopentenyl]benzaldehyde 
• 280584-60-3 (E,E)-2-(1-Methyl-2,4-diphenylbuta-1,3-dienyl)benzaldehyde 
• 280584-52-3 2-(2-Ethenylcyclopentenyl)benzaldehyde 
• 280584-56-7 2-[2-(2-Methylprop-1-enyl)cyclopentenyl]benzaldehyde 
• 280584-62-5 (E,E)-2-[1-Methyl-2-phenyl-4-(p-tolyl)buta-1,3-dienyl]benzaldehyde 
• 95752-86-6 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzaldehyde 

Relevant articles and documents

Annulative Morita-Baylis-Hillman reaction to synthesise chiral dibenzocycloheptanes

We describe the first metal-free and organocatalytic strategy to access highly functionalised dibenzocycloheptanesviaa phosphine-promoted annulative Morita-Baylis-Hillman (MBH) reaction. The method is manipulated to access to chiral dibenzocycloheptanes as well. This work represents a rare entry for the construction of seven-membered carbocyclesviathe MBH route. The realisation of several bioactive molecules possessing the dibenzocycloheptane core makes this an attractive strategy.

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.

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.