139962-95-1

Basic information

• Product Name: 4-Methoxy-2-formylphenylboronic acid
• Synonyms: 2-FORMYL-4-METHOXYPHENYLBORONIC ACID;4-METHOXY-2-FORMYLBENZENEBORONIC ACID;4-METHOXY-2-FORMYLPHENYLBORONIC ACID;AKOS BRN-0106;RARECHEM AH PB 0117;2-Formyl-4-methoxybenzeneboronic acid;2-Formyl-4-Methoxyphenylboroni;4-Methoxy-2-formylphenylboronic acid,97%
• CAS NO: 139962-95-1
• Molecular Formula: C₈H₉BO₄
• Molecular Weight: 179.97
• Product Categories: Boronic acids;Heterocyclic Compounds;Aldehyde;Aryl;Organoborons
• Mol File: 139962-95-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 148 °C
• Boiling Point: 395.238 °C at 760 mmHg
• Flash Point: 192.833 °C
• Appearance: white to light yellow powder
• Density: 1.26 g/cm³
• Vapor Pressure: 5.89E-07mmHg at 25°C
• Refractive Index: 1.537
• Storage Temp.: 0-6°C
• Solubility: soluble in Methanol
• PKA: 8.61±0.53(Predicted)
• CAS DataBase Reference: 4-Methoxy-2-formylphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methoxy-2-formylphenylboronic acid(139962-95-1)
• EPA Substance Registry System: 4-Methoxy-2-formylphenylboronic acid(139962-95-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• HazardClass: IRRITANT, KEEP COLD
• Hazardous Substances Data: 139962-95-1(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow powder

Uses

suzuki reaction

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

Upstream product

• 98015-07-7 2-Bromo-5-methoxybenzaldehyde ethylene glycol acetal 
• 5419-55-6 Triisopropyl borate 
• 121-43-7 Trimethyl borate 
• 181780-66-5 1-bromo-2-(dimethoxymethyl)-4-methoxybenzene 
• 1132669-90-9 5-methoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde 
• 591-31-1 3-methoxy-benzaldehyde 
• 19614-12-1 2-bromo-5-methoxybenzyl bromide 
• 27060-75-9 4-bromo-3-methylanisole 
• 7507-86-0 2-bromo-5-methoxy-benzaldehyde 
• 1186304-21-1 2-(2-bromo-5-methoxyphenyl)-1,3-dioxane 

Downstream Products

• 354529-43-4 3-(2-Formyl-4-methoxyphenyl)dibenzo[b,d]thiophene 
• 485824-20-2 1-(2-formyl-4-methoxyphenyl)dibenzothiophene 
• 671780-73-7 5-methoxy-2-(1,4-dimethoxynaphthalen-2-yl)benzaldehyde 
• 681215-17-8 7-(2-formyl-4-methoxyphenyl)-5,6-dihydro-4H-benz[de]anthracene 
• 830328-51-3 C₄₀H₂₈N₂O₄ 
• 958002-18-1 1H-indole-6-carboxylic acid, 3-cyclohexyl-2-(2-formyl-4-methoxyphenyl)-, 1,1-dimethylethyl ester 
• 760206-01-7 2-[(7bR,11aS)-1,2,7b,8,9,10,11,11a-octahydro-4H-pyrido[4,3-b][1,4]thiazepino[6,5,4-hi]indol-6-yl]-5-methoxybenzaldehyde, Trifluoroacetic Acid Salt 
• 313667-20-8 tert-butyl (6AS,10AR)-2-(2-formyl-4-methoxyphenyl)-4,5,7,8,10,10a-hexahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indole-9(6AH)-carboxylate 
• 313671-76-0 tert-butyl (8AS,12AR)-2-(2-formyl-4-methoxyphenyl)-4,5,6,7,8a,9,10,11,12,12a-decahydroazepino[3,2,1-hi]pyrido[4,3-b]indole-11(8AH)-carboxylate 
• 313672-05-8 tert-butyl (7AS,11AR)-2-(2-formyl-4-methoxyphenyl)-5,6,7a,8,9,10,11,11a-octahydro-4H-pyrido[3',4':4,5]pyrrolo[3,2,1-ij]quinoline-10(7AH)-carboxylate 
• 762263-92-3 (2-(hydroxymethyl)-4-methoxyphenyl)boronic acid 
• 902147-82-4 methyl 11-cyclohexyl-6-hydroxy-8-methoxy-6H-isoindolo[2,1-a]indole-3-carboxylate 
• 914497-93-1 tert-butyl 6-cyclohexyl-5-(2-formyl-4-methoxyphenyl)-4-(2-methoxy-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate 
• 902148-53-2 11-cyclohexyl-N-[(dimethylamino)sulfonyl]-6-hydroxy-8-methoxy-6H-isoindolo[2,1-a]indole-3-carboxamide 

Relevant articles and documents

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.

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.

Highly fluorescent, π-extended indenopyrido[2,1-a]isoindolone derivatives prepared by a palladium-catalysed cascade reaction

A new family of heterocyclic pentacyclic compounds have been prepared by a cascade reaction involving 2,5-dihalopyridines and (2-formylphenyl)boronic acids. Most of the compounds exhibit high quantum yields of fluorescence in dichloromethane. In some cases, small changes in the substitution pattern caused fluorescence quenching. To rationalize this effect, a detailed photophysical study combined with electrochemical and computational studies was performed on four representative derivatives. It appears that the fluorescence quenching is caused by a thermally activated non-radiative deactivation process that can be prevented in a rigid matrix such as ethanol at 77 K or a PMMA polymer.