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

• 112627-02-8 (2-Br₂CHC₆H₄)B(OH)2 
• 121-43-7 Trimethyl borate 
• 35849-09-3 o-bromobenzaldehyde dimethyl acetal 
• 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 
• 34824-58-3 2-(2-bromophenyl)-1,3-dioxolan 
• 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

• 19203-45-3 Boronophthalidyl-essigsaeure 
• 91783-81-2 1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborole-3-carbonitrile 
• 176690-44-1 2-(pyridin-3-yl)benzaldehyde 
• 176526-00-4 2-(pyridin-4-yl)benzaldehyde 
• 213881-52-8 ethyl 3-(2-formylphenyl)-1-methyl-1H-2-indolecarboxylate 
• 184041-20-1 N-(3-methyl-5-isoxazolyl)-5-(2-formylphenyl)thiophene-2-sulfonamide 
• 476172-03-9 2-(5-methoxy-2-methyl-3-oxo-2,3-dihydropyridazin-4-yl)benzaldehyde 
• 566198-45-6 5-(2-FORMYLPHENYL)-PICOLINIC ACID 
• 16191-28-9 2-(4-methylphenyl)benzaldehyde 
• 681215-16-7 7-(2-formylphenyl)-5,6-dihydro-4H-benz[de]anthracene 
• 764665-05-6 benzyl [2-(2'-formyl-4,5-dimethoxybiphenyl-2-yl)ethyl]carbamate 

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.

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.