1256346-05-0

Basic information

• Product Name: 3-Ethoxy-5-methylphenylboronic acid
• Synonyms: 3-Ethoxy-5-methylphenylboronic acid
• CAS NO: 1256346-05-0
• Molecular Formula: C₉H₁₃BO₃
• Molecular Weight: 180.00872
• Mol File: 1256346-05-0.mol

Chemical Properties

• Boiling Point: 354.1±52.0 °C(Predicted)
• Appearance: /
• Density: 1.11±0.1 g/cm3(Predicted)
• Storage Temp.: Room temperature.
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 8.24±0.10(Predicted)
• CAS DataBase Reference: 3-Ethoxy-5-methylphenylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Ethoxy-5-methylphenylboronic acid(1256346-05-0)
• EPA Substance Registry System: 3-Ethoxy-5-methylphenylboronic acid(1256346-05-0)

Safety Data

• Hazardous Substances Data: 1256346-05-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Ethoxy-5-methylphenylboronic acid is used as a reagent in organic synthesis for its ability to form carbon-carbon bonds in organic molecules. It is particularly useful in Suzuki-Miyaura coupling reactions, a popular method for creating these bonds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 3-Ethoxy-5-methylphenylboronic acid is used as a building block for the development of new drugs. Its unique structure and reactivity make it a valuable component in the synthesis of pharmaceutical compounds.
Used in Pharmaceutical Applications:
3-Ethoxy-5-methylphenylboronic acid has been studied for its potential pharmaceutical applications, particularly in the development of new drugs for conditions such as cancer and diabetes. Its ability to form carbon-carbon bonds and its reactivity make it a promising candidate for the creation of novel therapeutic agents.
Used in Drug Discovery:
3-Ethoxy-5-methylphenylboronic acid plays a crucial role in drug discovery, as it can be used to create new drug candidates with potential therapeutic effects. Its versatility in organic synthesis and medicinal chemistry allows researchers to explore its potential in treating various diseases and conditions.

Upstream product

• 504-15-4 orcinol 
• 889659-69-2 3-hydroxy-5-methylphenyl trifluoromethanesulfonate 
• 889659-70-5 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 
• 75-03-6 ethyl iodide 

Downstream Products

• 1402585-77-6 tert-butyl (1-(3-ethoxy-5-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylcarbamate 

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.