1106869-99-1

Basic information

• Product Name: 3-FORMYL-4-METHYLPHENYLBORONIC ACID
• Synonyms: 3-FORMYL-4-METHYLPHENYLBORONIC ACID
• CAS NO: 1106869-99-1
• Molecular Formula: C₈H₉BO₃
• Molecular Weight: 163.97
• Product Categories: Boronic acid;Aryl;Organoborons
• Mol File: 1106869-99-1.mol

Chemical Properties

• Boiling Point: 356.5±52.0 °C(Predicted)
• Appearance: /
• Density: 1.20±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 8.10±0.10(Predicted)
• CAS DataBase Reference: 3-FORMYL-4-METHYLPHENYLBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-FORMYL-4-METHYLPHENYLBORONIC ACID(1106869-99-1)
• EPA Substance Registry System: 3-FORMYL-4-METHYLPHENYLBORONIC ACID(1106869-99-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 1106869-99-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-Formyl-4-methylphenylboronic acid is used as a building block for the synthesis of complex organic compounds due to its ability to form stable boronate complexes with various organic molecules. This property makes it a valuable component in the creation of intricate molecular structures and contributes to the advancement of organic chemistry.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 3-Formyl-4-methylphenylboronic acid is used as a reagent in the development of novel drugs. Its unique chemical properties and ability to participate in cross-coupling reactions facilitate the design and synthesis of new pharmaceutical compounds with potential therapeutic applications.
Used in Cross-Coupling Reactions:
3-Formyl-4-methylphenylboronic acid is utilized as a reagent in cross-coupling reactions, a class of chemical reactions that are fundamental in organic synthesis. Its role in these reactions is crucial for the formation of carbon-carbon and carbon-heteroatom bonds, which are essential in constructing a wide range of organic molecules.
Used in the Preparation of Aryl Aldehydes:
As a reagent, 3-Formyl-4-methylphenylboronic acid is employed in the preparation of aryl aldehydes, which are important intermediates in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and fragrances. Its use in this process highlights its versatility and importance in the synthesis of valuable organic molecules.
Used as a Catalyst in Organic Reactions:
3-Formyl-4-methylphenylboronic acid also serves as a catalyst in certain organic reactions, enhancing the rate of these reactions and improving the overall efficiency of the synthesis process. Its catalytic properties contribute to its utility in various chemical transformations, further expanding its applications in the field of organic chemistry.

Upstream product

• 688-74-4 boric acid tributyl ester 
• 7732-18-5 water 

Downstream Products

• 1544673-61-1 2-[2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]isoindoline-1,3-dione 
• 1544673-80-4 [2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanamine 
• 1544673-46-2 [2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanol 
• 1352132-34-3 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde 

Relevant articles and documents

Preparation method of 3-formyl-4-methylphenylboronic acid

The invention discloses a preparation method of 3-formyl-4-methylphenylboronic acid. The method comprises the following steps of: adding 2-methyl-5-bromobenzaldehyde into a reaction vessel under the protection of nitrogen, adding a mixed solution of toluene and ethylene glycol, adding p-toluenesulfonic acid, carrying out heating reflux reaction, then performing desolventizing and rectifying to obtain a pure product of 2-methyl-5-bromobenzaldehyde diethyl acetal; dropwise adding tetrahydrofuran containing the pure product of 2-methyl-5-bromobenzaldehyde diethyl acetal and tributyl borate into tetrahydrofuran containing magnesium chips under the protection of nitrogen, carrying out heating reflux reaction, adding sulfuric acid to adjust the pH value to 2-4 after the reaction is finished, andperforming stirring to obtain a solution containing white solid; and adding an organic solvent into the obtained solution containing the white solid for extraction, combining all organic phases, carrying out reduced pressure rectification, recovering the solvent, and carrying out kettle bottom solid phase recrystallization to obtain the 3-formyl-4-methylphenylboronic acid. The method has the advantages of wide raw material sources, low production cost and mild reaction conditions, and is suitable for large-scale production and application.

Preparation method of 3-aldehyde-4-methylphenylboronic acid

The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of 3-aldehyde-4-methylphenylboronic acid. The preparation method comprises the following steps: with 2-methyl-5-bromobenzaldehyde as a raw material, performing a reaction on the 2-methyl-5-bromobenzaldehyde and alcohol to obtain acetal, performing a lithium halide exchange reaction on the acetal and a lithiation reagent at low temperature to obtain a phenyl lithium compound, and performing a reaction on the obtained phenyl lithium compound and a boronation reagent to obtain phenyl boronate; then hydrolyzing by using hydrochloric acid with the mass concentration of 10% to obtain crude 3-aldehyde-4-methylphenylboronic acid, and finally purifying to obtain pure 3-aldehyde-4-methylphenylboronic acid, wherein in the reaction, tetrahydrofuran is used as a reaction solvent. The preparation method of the 3-aldehyde-4-methylphenylboronic acid has the advantages as follows: used raw materials are cheap and easy to obtain, the reaction condition is mild, the posttreatment operation is simple, the production cost is relatively low, the yield is high, the reaction cost is reduced,and the preparation method is suitable for industrial production.