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

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

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

• 112627-02-8 (2-Br₂CHC₆H₄)B(OH)2 
• 380151-85-9 2-(2'-formylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 16419-60-6 2-Methylphenylboronic acid 
• 34824-58-3 2-(2-bromophenyl)-1,3-dioxolan 
• 121-43-7 Trimethyl borate 
• 932-31-0 ortho-tolylmagnesium bromide 
• 7294-50-0 tri-o-tolylboroxine 
• 6630-33-7 ortho-bromobenzaldehyde 
• 5419-55-6 Triisopropyl borate 
• 1229227-01-3 C₁₈H₁₂B₃Br₃O₃ 
• 68-12-2 N,N-dimethyl-formamide 
• 35849-09-3 o-bromobenzaldehyde dimethyl acetal 

Downstream Products

• 19203-45-3 Boronophthalidyl-essigsaeure 
• 91783-81-2 1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborole-3-carbonitrile 
• 129265-61-8 2,9-bis-1,10-phenanthroline 
• 99902-07-5 2-(2-thienyl)benzaldehyde 
• 99902-03-1 2-(thien-3-yl)benzaldehyde 
• 176690-44-1 2-(pyridin-3-yl)benzaldehyde 
• 176526-00-4 2-(pyridin-4-yl)benzaldehyde 
• 870703-82-5 tert-butyl (2'-formyl-[1,1'-biphenyl]-4-yl)carbamate 
• 205823-24-1 methyl 2'-formyl-(1,1'-biphenyl)-4-carboxylate 
• 16231-67-7 methyl 2'-formyl-[1,1'-biphenyl]-2-carboxylate 

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.

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.

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.

Quinoline diamine-containing fourth subgroup metal complex and application thereof

The invention relates to the technical field of olefin polymerization catalysts, and particularly discloses a quinoline diamine-containing fourth subgroup metal complex and application thereof. The quinoline diamine-containing fourth subgroup metal complex has the following structure: the quinoline diamine-containing fourth subgroup metal complex provided by the invention can catalyze ethylene homopolymerisation with high activity to obtain polyethylene with high molecular weight, and catalyze ethylene and [alpha]-olefin with high activity to copolymerize to generate a copolymer with medium to high molecular weight and insertion amount; and therefore, the problem that an existing olefin polymerization catalyst cannot generate a high-molecular-weight polymer while improving the catalytic activity is solved, and the olefin polymerization catalyst has a wide application prospect.

Tris(2-carboxyethyl)phosphine promotes hydrolysis of iminoboronates

Iminoboronates are stable and formed fast. Their B[sbnd]N bonds could be reverted by some endogenous biological molecules. The reversible characteristic attracts significant attention in biological and chemical fields. Although synthesis of iminoboronates is well-studied, less efforts have been devoted to disconnecting the units. Here, a series of selected compounds were screened to evaluate their hydrolytic capability of iminoboronates by 1H NMR or 11B NMR detection. Tris(2-carboxyethyl)phosphine (TCEP), was emerged as an excellent reagent, which decomposed most iminoboronates in short time with high yields. In addition, TCEP is also able to hydrolyze hydrazones and oximes with moderate yields.

A process for preparing aldehyde group benzene boric acid

The invention discloses a method for preparing formyl phenylboronic acid, which comprises the following steps: heating halogenated phenylboronic acid in toluene or heptane under reflux for dewatering to form a tripolymer, mixing the tripolymer with dimethylformamide, dropwisely adding n-butyllithium at low temperature to react by a one-pot process, hydrolyzing with hydrochloric acid, and recrystallizing to obtain the formyl phenylboronic acid. The method is simple to operate, avoids the process of separating the intermediate after formyl protection in the conventional technique, has high universality, can obtain favorable yield for ortho-, meta- and para- formyl phenylboronic acids, and is beneficial to scale-up production.

Synthesis of naphthalene ring derivatives and Benzoheterocycles the method of the compound

The invention discloses a method for synthesizing naphthalene derivative and benzo-heterocycle compounds. The method is realized by promoting a reaction similar to Mortia-Baylis-Hillman between aryl aldehyde having alpha, beta-unsaturated ester on ortho-position and ketone compounds under the catalysis action of tertiary amine and tertiary phosphine organic small molecular catalysts, so as to remove a molecule of H2O, so that the naphthalene derivative or benzo-heterocycle compounds are generated. The method disclosed by the invention is simple in operation step, cheap and easily available in adopted catalysts and harmless to environment, and a series of naphthalene derivative and benzo-heterocycle compounds are synthesized with relatively high yield.

Boronic acids facilitate rapid oxime condensations at neutral pH

We report here the discovery and development of boron-assisted oxime formation as a powerful connective reaction for chemical biology. Oximes proximal to boronic acids form in neutral aqueous buffer with rate constants of more than 104 M-1