253280-01-2

Basic information

• Product Name: Boronic acid, (2-methoxyphenyl)-, dimethyl ester (9CI)
• Synonyms: Boronic acid, (2-methoxyphenyl)-, dimethyl ester (9CI)
• CAS NO: 253280-01-2
• Molecular Formula: C₉H₁₃BO₃
• Molecular Weight: 180.00872
• Product Categories: BORONICACID
• Mol File: 253280-01-2.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Boronic acid, (2-methoxyphenyl)-, dimethyl ester (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Boronic acid, (2-methoxyphenyl)-, dimethyl ester (9CI)(253280-01-2)
• EPA Substance Registry System: Boronic acid, (2-methoxyphenyl)-, dimethyl ester (9CI)(253280-01-2)

Safety Data

• Hazardous Substances Data: 253280-01-2(Hazardous Substances Data)

Upstream product

• 121-43-7 Trimethyl borate 
• 100-66-3 methoxybenzene 
• 578-57-4 2-bromoanisole 
• 16750-63-3 2-methoxyphenylmagnesium bromide 
• 67-56-1 methanol 
• 90-04-0 2-methoxy-phenylamine 
• 766-51-8 2-Chloroanisole 

Downstream Products

• 5720-06-9 2-Methoxyphenylboronic acid 
• 173204-11-0 methyl 3-<2-<(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)oxy>phenyl>phenylacetate 
• 724700-58-7 {3-[5-(3-aminopropyl)-2-(α-D-mannopyranosyloxy)phenyl]phenyl}acetic acid 
• 508209-70-9 methyl {3-[5-(3-bromopropyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate 
• 508209-72-1 methyl {3-[5-(3-aminopropyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate 
• 508209-69-6 methyl {3-[5-(3-bromopropionyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate 
• 508209-71-0 methyl {3-[5-(3-azidopropyl)-2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]phenyl}acetate 
• 508209-77-6 methyl 3-[2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)-5-(3-phthalimidylpropyl)phenyl]phenylacetate 
• 190788-60-4 pinacol 2-anisylboronate 

Relevant articles and documents

Amine-borane complexes: Air- and moisture-stable partners for palladium-catalyzed borylation of aryl bromides and chlorides

A method for using amine-borane complexes directly in palladium catalyzed borylation has been developed. The reaction proceeds through the sequential formation of a boronium species followed by deprotonation leading to the aminoborane. This reagent is then directly used in the borylation process leading, after work-up, to various boronic acid derivatives. The reaction was applied to (hetero)aryl triflates, iodides, bromides and chlorides.

Borylation using group IV metallocene under mild conditions

A borylation reaction of aromatic diazonium salts has been optimized using titanocene and zirconocene derivatives as catalysts. The reaction employs diisopropylaminoborane as a borylating agent and proceeds smoothly at room temperature to provide arylboronates after methanolysis and transesterification with pinacol. The reaction mechanism has been found to proceed via a radical pathway.

Mild and selective synthesis of an aryl boronic ester by equilibration of mixtures of boronic and borinic acid derivatives

Quenching of aryl Grignard reagents with 2-isopropoxy-4,4,5,5-tetramethyl- 1,3,2-dioxaborolane (isopropyl pinacol borate) under noncryogenic conditions can lead to mixtures of the corresponding boronic ester along with, generally undesired, borinic acid derivatives. We have found that in certain cases gentle heating of the crude reaction mixtures leads to complete equilibration to give the borinic esters as the sole product which can then be isolated in high yield. This novel equilibration can reduce the need for use of cryogenic conditions or large excesses of reagents to obtain selectivity during boronic ester syntheses.