1256355-61-9

Basic information

• Product Name: 3-(Benzyloxy)-5-methylphenylboronic acid
• Synonyms: 3-(Benzyloxy)-5-methylphenylboronic acid
• CAS NO: 1256355-61-9
• Molecular Formula: C14H15BO3
• Molecular Weight: 242.0781
• Mol File: 1256355-61-9.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: Room temperature.
• CAS DataBase Reference: 3-(Benzyloxy)-5-methylphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(Benzyloxy)-5-methylphenylboronic acid(1256355-61-9)
• EPA Substance Registry System: 3-(Benzyloxy)-5-methylphenylboronic acid(1256355-61-9)

Safety Data

• Hazardous Substances Data: 1256355-61-9(Hazardous Substances Data)

Usage

General Description

3-(Benzyloxy)-5-methylphenylboronic acid is an organic compound that belongs to the class of boronic acids. It consists of a boronic acid group attached to a phenyl ring with a benzyloxy and a methyl group bonded to the ring. 3-(Benzyloxy)-5-methylphenylboronic acid is commonly used in organic synthesis as a reagent for Suzuki-Miyaura coupling reactions, which is a widely-used method for carbon-carbon bond formation. It is also used in the development of pharmaceuticals and materials science. Additionally, it has been reported to exhibit anti-cancer activity, making it a potentially valuable compound in the field of medicinal chemistry.

Upstream product

• 504-15-4 orcinol 
• 889659-69-2 3-hydroxy-5-methylphenyl trifluoromethanesulfonate 

Relevant articles and documents

Enantiodivergent Fluorination of Allylic Alcohols: Data Set Design Reveals Structural Interplay between Achiral Directing Group and Chiral Anion

Enantioselectivity values represent relative rate measurements that are sensitive to the structural features of the substrates and catalysts interacting to produce them. Therefore, well-designed enantioselectivity data sets are information rich and can provide key insights regarding specific molecular interactions. However, if the mechanism for enantioselection varies throughout a data set, these values cannot be easily compared. This premise, which is the crux of free energy relationships, exposes a challenging issue of identifying mechanistic breaks within multivariate correlations. Herein, we describe an approach to addressing this problem in the context of a chiral phosphoric acid catalyzed fluorination of allylic alcohols using aryl boronic acids as transient directing groups. By designing a data set in which both the phosphoric and boronic acid structures were systematically varied, key enantioselectivity outliers were identified and analyzed. A mechanistic study was executed to reveal the structural origins of these outliers, which was consistent with the presence of several mechanistic regimes within the data set. While 2- and 4-substituted aryl boronic acids favored the (R)-enantiomer with most of the studied catalysts, meta-alkoxy substituted aryl boronic acids resulted in the (S)-enantiomer when used in combination with certain (R)-phosphoric acids. We propose that this selectivity reversal is the result of a lone pair-π interaction between the substrate ligated boronic acid and the phosphate. On the basis of this proposal, a catalyst system was identified, capable of producing either enantiomer in high enantioselectivity (77% (R)-2 to 92% (S)-2) using the same chiral catalyst by subtly changing the structure of the achiral boronic acid.