40138-18-9

Basic information

• Product Name: 5-Methoxy-2-formylphenylboronic acid
• Synonyms: AKOS BRN-0107;5-METHOXY-2-FORMYLBENZENEBORONIC ACID;5-METHOXY-2-FORMYLPHENYLBORONIC ACID;2-FORMYL-5-METHOXYPHENYLBORONIC ACID;2-Formyl-5-Methoxyphenylboroni;5-METHOXY-2-FORMYLPHENYLBORONIC ACID 96%;5-Methoxy-2-formylphenylboronic acid,98%;2-Formyl-5-methoxybenzeneboronic acid
• CAS NO: 40138-18-9
• Molecular Formula: C₈H₉BO₄
• Molecular Weight: 179.97
• Product Categories: Substituted Boronic Acids;Boronic acids;Heterocyclic Compounds;Aldehyde;Aryl;Organoborons
• Mol File: 40138-18-9.mol
• Article Data: 2

Chemical Properties

• Melting Point: 155-160 °C
• Boiling Point: 417.967 °C at 760 mmHg
• Flash Point: 206.579 °C
• Appearance: Yellowish-beige powder
• Density: 1.26 g/cm³
• Vapor Pressure: 9.83E-08mmHg at 25°C
• Refractive Index: 1.537
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 7.75±0.53(Predicted)
• CAS DataBase Reference: 5-Methoxy-2-formylphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methoxy-2-formylphenylboronic acid(40138-18-9)
• EPA Substance Registry System: 5-Methoxy-2-formylphenylboronic acid(40138-18-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• HazardClass: IRRITANT, KEEP COLD
• Hazardous Substances Data: 40138-18-9(Hazardous Substances Data)

Usage

Description

5-Methoxy-2-formylphenylboronic acid is an organic compound that features a boron atom bonded to a phenyl ring with a methoxy group at the 5th position and a formyl group at the 2nd position. 5-Methoxy-2-formylphenylboronic acid is known for its versatile reactivity and is commonly utilized in various chemical reactions and synthesis processes.

Uses

Used in Suzuki Reaction:
5-Methoxy-2-formylphenylboronic acid is used as a reagent in the Suzuki reaction, a widely employed method for the formation of carbon-carbon bonds, particularly in the synthesis of biaryl compounds. 5-Methoxy-2-formylphenylboronic acid's boronic acid functionality allows it to participate in palladium-catalyzed cross-coupling reactions, enabling the formation of new carbon-carbon bonds with a wide range of organic substrates.
Used in Total Synthesis of Laetevirenol A:
In the pharmaceutical industry, 5-Methoxy-2-formylphenylboronic acid is used as a reagent for the total synthesis of laetevirenol A, a natural product with potential biological activities. 5-Methoxy-2-formylphenylboronic acid's unique structure allows it to undergo intramolecular Friedel-Crafts alkylation, a key step in the construction of the complex molecular framework of laetevirenol A.

InChI:InChI=1/C8H9BO4/c1-13-7-3-2-6(5-10)8(4-7)9(11)12/h2-5,11-12H,1H3

Upstream product

• 1196474-59-5 4-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 1447360-34-0 2-(6-bromopyridin-3-yl)-4-methoxybenzaldehyde 
• 1196474-59-5 4-methoxy-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde 
• 1610973-54-0 2-benzyl-4-methoxybenzaldehyde 
• 1381889-70-8 C₂₃H₂₂O₅ 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 1285527-75-4 C₂₀H₁₉NO₃ 
• 1181214-26-5 4-methoxy-2-[1-(4-trifluoromethoxyphenyl)-1H-imidazol-4-yl]-benzaldehyde 
• 53948-10-0 aristololactam BIII 
• 744251-64-7 C₂₀H₁₈N₂O₄ 

Relevant articles and documents

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.