929626-18-6

Basic information

• Product Name: 3-(METHOXYCARBONYL)-5-METHYLPHENYLBORONIC ACID
• Synonyms: 3-(METHOXYCARBONYL)-5-METHYLPHENYLBORONIC ACID
• CAS NO: 929626-18-6
• Molecular Formula: C₉H₁₁BO₄
• Molecular Weight: 193.993
• Mol File: 929626-18-6.mol

Chemical Properties

• Boiling Point: 385.2±52.0 °C(Predicted)
• Appearance: /
• Density: 1.21±0.1 g/cm3(Predicted)
• PKA: 7.83±0.10(Predicted)
• CAS DataBase Reference: 3-(METHOXYCARBONYL)-5-METHYLPHENYLBORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(METHOXYCARBONYL)-5-METHYLPHENYLBORONIC ACID(929626-18-6)
• EPA Substance Registry System: 3-(METHOXYCARBONYL)-5-METHYLPHENYLBORONIC ACID(929626-18-6)

Safety Data

• Hazardous Substances Data: 929626-18-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-(METHOXYCARBONYL)-5-METHYLPHENYLBORONIC ACID is used as a reagent for the formation of carbon-carbon and carbon-heteroatom bonds, facilitating the synthesis of complex organic molecules.
Used in Medicinal Chemistry:
In the pharmaceutical industry, 3-(METHOXYCARBONYL)-5-METHYLPHENYLBORONIC ACID is used as a key intermediate in the production of pharmaceuticals, contributing to the development of new drugs.
Used in Agrochemicals:
3-(METHOXYCARBONYL)-5-METHYLPHENYLBORONIC ACID is also utilized in the agrochemical industry for the synthesis of compounds that have applications in agriculture, such as pesticides and herbicides.
Used in Suzuki-Miyaura Cross-Coupling Reactions:
3-(METHOXYCARBONYL)-5-METHYLPHENYLBORONIC ACID is used as a coupling partner in Suzuki-Miyaura cross-coupling reactions, a widely employed method in organic chemistry for the formation of carbon-carbon bonds, particularly useful for the synthesis of biologically active molecules and materials with specific properties.

Upstream product

• 99-36-5 1-methoxycarbonyl-3-methylbenzene 
• 73183-34-3 bis(pinacol)diborane 
• 929626-17-5 methyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 

Downstream Products

• 660416-38-6 methyl 3-fluoro-5-methylbenzoate 
• 1261650-22-9 methyl 3-methyl-5-(trifluoromethoxy)benzoate 

Relevant articles and documents

FLUORINATION OF ORGANIC COMPOUNDS

Methods for fluorinating organic compounds are described herein.

Fluorination of boronic acids mediated by silver(I) Triflate

A regiospecific Ag-mediated fluorination reaction of aryl- and alkenylboronic acids and esters Is reported. The fluorination reaction uses commercially available reagents, does not require the addition of exogenous ligands, and can be performed on a multigram scale. This report discloses the first practical reaction sequence from arylboronic acid to aryl fluorides.

Arenes to anilines and aryl ethers by sequential iridium-catalyzed borylation and copper-catalyzed coupling

(Chemical Equation Presented) N-Alkyl- and N-arylanilines were synthesized from arenes by a two-step sequence of iridium-catalyzed borylation and copper-catalyzed coupling with amines. Diaryl ethers were obtained by a related sequence of arene borylation, followed by coupling with phenols. In particular, 3,5-disubstituted arylamines and aryl ethers were prepared by initiating this sequence with meta-substituted arenes.

One-pot synthesis of arylboronic acids and aryl trifluoroborates by Ir-catalyzed borylation of arenes

(Chemical Equation Presented) The synthesis of arylboronic acids and aryl trifluoroborates in a one-pot sequence by Ir-calalyzed borylation of arenes is reported. To prepare the arylboronic acids, the Ir-catalyzed borylation is followed by oxidative cleavage of the boronic ester with NaIO4. To prepare the aryltrifluoroborate, the Ir-catalyzed borylation is followed by displacement of pinacol by KHF2. These two-step sequences give products that are more reactive toward subsequent chemistry than the initially formed pinacol boronates.