Cas no 693774-55-9 (2,6-Dimethylpyridin-3-ylboronic acid)

2,6-Dimethylpyridin-3-ylboronic acid is a boronic acid derivative featuring a pyridine core substituted with methyl groups at the 2- and 6-positions. This compound is widely utilized as a key intermediate in Suzuki-Miyaura cross-coupling reactions, enabling the synthesis of complex biaryl and heteroaryl structures. Its sterically hindered pyridine ring enhances selectivity in coupling reactions, while the boronic acid group ensures reactivity with various electrophilic partners. The compound is particularly valuable in pharmaceutical and agrochemical research for constructing nitrogen-containing heterocycles. It exhibits good stability under standard handling conditions and is compatible with a range of solvents, making it a versatile reagent for organic synthesis.
2,6-Dimethylpyridin-3-ylboronic acid structure
693774-55-9 structure
Product Name:2,6-Dimethylpyridin-3-ylboronic acid
CAS No:693774-55-9
MF:C7H10BNO2
MW:150.970801830292
MDL:MFCD07437925
CID:502603
PubChem ID:2763093
Update Time:2025-10-29

2,6-Dimethylpyridin-3-ylboronic acid Chemical and Physical Properties

Names and Identifiers

    • 2,6-Dimethylpyridin-3-ylboronic acid
    • (2,6-dimethylpyridin-3-yl)boronic acid
    • 2,6-Dimethylpyridine-3-boronic acid
    • Boronic acid,B-(2,6-dimethyl-3-pyridinyl)-
    • 2,5-DIMETHYL-1-HEXENE
    • 2,6-dimethyl-3-pyridinylboronic acid
    • 2,6-DIMETHYL-PYRIDINE-3-BORONIC ACID
    • (2,6-dimethyl-3-pyridinyl)boronic acid
    • Boronic acid, (2,6-dimethyl-3-pyridinyl)-
    • OZGKXVIJOMDZCP-UHFFFAOYSA-N
    • FCH856150
    • 2,6-Domethylpyridine-3-boronic acid
    • AB41961
    • (2,6-dim
    • MDL: MFCD07437925
    • Inchi: 1S/C7H10BNO2/c1-5-3-4-7(8(10)11)6(2)9-5/h3-4,10-11H,1-2H3
    • InChI Key: OZGKXVIJOMDZCP-UHFFFAOYSA-N
    • SMILES: OB(C1=CC=C(C)N=C1C)O

Computed Properties

  • Exact Mass: 151.08000
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 132
  • Topological Polar Surface Area: 53.4

Experimental Properties

  • PSA: 53.35000
  • LogP: -0.62180

2,6-Dimethylpyridin-3-ylboronic acid Security Information

  • Hazard Category Code: 22
  • Hazardous Material Identification: Xn

2,6-Dimethylpyridin-3-ylboronic acid Pricemore >>

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Additional information on 2,6-Dimethylpyridin-3-ylboronic acid

2,6-Dimethylpyridin-3-ylboronic Acid: A Comprehensive Overview

In the realm of organic chemistry, 2,6-Dimethylpyridin-3-ylboronic acid (CAS No. 693774-55-9) stands out as a significant compound with diverse applications and intriguing chemical properties. This compound, also referred to as DMPy-B(OH)?, belongs to the family of organoboron compounds, which have garnered substantial attention in recent years due to their unique reactivity and versatility in various chemical reactions.

The structure of 2,6-Dimethylpyridin-3-ylboronic acid comprises a pyridine ring substituted with two methyl groups at the 2 and 6 positions and a boronic acid group at the 3 position. This substitution pattern imparts specific electronic and steric properties to the molecule, making it highly suitable for applications in cross-coupling reactions, such as the Suzuki-Miyaura coupling. These reactions are pivotal in organic synthesis, enabling the construction of complex molecular architectures with precision and efficiency.

Recent advancements in the synthesis of DMPy-B(OH)? have focused on optimizing reaction conditions to enhance yield and purity. For instance, researchers have explored the use of microwave-assisted synthesis and continuous-flow reactors to streamline the production process. These innovations not only improve scalability but also reduce environmental impact by minimizing waste generation.

The chemical properties of 2,6-Dimethylpyridin-3-ylboronic acid are heavily influenced by its boronic acid functionality. Boronic acids are known for their ability to undergo nucleophilic substitution reactions, particularly under basic conditions. This reactivity is exploited in various catalytic processes, including those involving palladium catalysts. The methyl substituents on the pyridine ring further modulate the electronic environment, enhancing the compound's stability and reactivity in specific reaction scenarios.

One of the most notable applications of DMPy-B(OH)? is in drug discovery and development. Its role as a building block in medicinal chemistry has been instrumental in designing bioactive molecules targeting various therapeutic areas. For example, recent studies have demonstrated its utility in synthesizing potential anticancer agents with high selectivity and efficacy.

In addition to its role in medicinal chemistry, 2,6-Dimethylpyridin-3-ylboronic acid finds applications in materials science. Its incorporation into polymer systems has been explored for developing advanced materials with tailored electronic properties. Researchers have reported promising results in synthesizing conductive polymers that exhibit enhanced charge transport capabilities.

From an environmental standpoint, the synthesis and use of DMPy-B(OH)? have been scrutinized for their sustainability profiles. Efforts are underway to develop eco-friendly synthesis routes that utilize renewable feedstocks and minimize energy consumption. These initiatives align with global trends toward greener chemical processes and circular economy principles.

In conclusion, 2,6-Dimethylpyridin-3-ylboronic acid (CAS No. 693774-55-9) is a multifaceted compound with significant potential across various domains of chemistry and materials science. Its unique structure, reactivity, and versatility continue to drive innovative research and development efforts worldwide.

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