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

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

Uses

Used in Organic Synthesis:
3-(Benzyloxy)-5-methylphenylboronic acid is used as a reagent in Suzuki-Miyaura coupling reactions, a widely-applied method for carbon-carbon bond formation. It plays a crucial role in the synthesis of complex organic molecules, facilitating the formation of new chemical bonds and contributing to the development of novel compounds.
Used in Pharmaceutical Development:
In the pharmaceutical industry, 3-(Benzyloxy)-5-methylphenylboronic acid is utilized in the development of new drugs. Its unique chemical structure allows it to be incorporated into various drug candidates, potentially enhancing their therapeutic properties and effectiveness in treating different medical conditions.
Used in Materials Science:
3-(Benzyloxy)-5-methylphenylboronic acid is also employed in the field of materials science. Its incorporation into various materials can impart specific properties, such as improved stability, enhanced reactivity, or unique physical characteristics, making it a valuable component in the development of advanced materials.
Used in Medicinal Chemistry:
3-(Benzyloxy)-5-methylphenylboronic acid has been reported to exhibit anti-cancer activity, making it a potentially valuable compound in the field of medicinal chemistry. Its ability to target and inhibit the growth of cancer cells highlights its potential as a therapeutic agent in cancer treatment, offering a promising avenue for further research and development.

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.