Cas no 1805042-99-2 (4,6-Dibromo-2-(difluoromethyl)-3-hydroxypyridine)

4,6-Dibromo-2-(difluoromethyl)-3-hydroxypyridine is a halogenated pyridine derivative with a difluoromethyl substituent at the 2-position and a hydroxyl group at the 3-position. This compound is of interest in pharmaceutical and agrochemical research due to its versatile reactivity, particularly in cross-coupling reactions and as a building block for heterocyclic synthesis. The presence of bromine atoms enhances its utility in further functionalization, while the difluoromethyl group contributes to metabolic stability and lipophilicity. The hydroxyl group provides a handle for additional modifications. Its well-defined structure and high purity make it suitable for applications in medicinal chemistry and material science, where precise molecular design is critical.
4,6-Dibromo-2-(difluoromethyl)-3-hydroxypyridine structure
1805042-99-2 structure
Product Name:4,6-Dibromo-2-(difluoromethyl)-3-hydroxypyridine
CAS No:1805042-99-2
MF:C6H3Br2F2NO
MW:302.898926973343
CID:4918261
Update Time:2025-06-12

4,6-Dibromo-2-(difluoromethyl)-3-hydroxypyridine Chemical and Physical Properties

Names and Identifiers

    • 4,6-Dibromo-2-(difluoromethyl)-3-hydroxypyridine
    • Inchi: 1S/C6H3Br2F2NO/c7-2-1-3(8)11-4(5(2)12)6(9)10/h1,6,12H
    • InChI Key: BQJOQZZPYWXIHR-UHFFFAOYSA-N
    • SMILES: BrC1C=C(N=C(C(F)F)C=1O)Br

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 1
  • Complexity: 161
  • XLogP3: 2.9
  • Topological Polar Surface Area: 33.1

4,6-Dibromo-2-(difluoromethyl)-3-hydroxypyridine Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
Alichem
A024004127-250mg
4,6-Dibromo-2-(difluoromethyl)-3-hydroxypyridine
1805042-99-2 97%
250mg
$646.00 2022-04-01
Alichem
A024004127-500mg
4,6-Dibromo-2-(difluoromethyl)-3-hydroxypyridine
1805042-99-2 97%
500mg
$999.60 2022-04-01
Alichem
A024004127-1g
4,6-Dibromo-2-(difluoromethyl)-3-hydroxypyridine
1805042-99-2 97%
1g
$1,696.80 2022-04-01

Additional information on 4,6-Dibromo-2-(difluoromethyl)-3-hydroxypyridine

Introduction to 4,6-Dibromo-2-(difluoromethyl)-3-hydroxypyridine (CAS No. 1805042-99-2)

4,6-Dibromo-2-(difluoromethyl)-3-hydroxypyridine, identified by the CAS number 1805042-99-2, is a specialized heterocyclic compound that has garnered significant attention in the field of pharmaceutical and agrochemical research. This compound belongs to the pyridine family, a class of nitrogen-containing heterocycles that are widely recognized for their diverse biological activities and utility in medicinal chemistry. The structural features of this molecule, including its bromo and difluoromethyl substituents, as well as the hydroxyl group, contribute to its unique chemical properties and potential applications.

The significance of 4,6-Dibromo-2-(difluoromethyl)-3-hydroxypyridine lies in its versatility as a building block for the synthesis of more complex molecules. In recent years, there has been a growing interest in developing novel pyridine derivatives for their pharmacological properties. The presence of bromine atoms makes this compound a valuable intermediate in cross-coupling reactions, such as Suzuki-Miyaura and Buchwald-Hartwig couplings, which are fundamental in constructing carbon-carbon bonds. These reactions are pivotal in the synthesis of biologically active compounds, including drugs and agrochemicals.

The difluoromethyl group is another critical feature of this compound. Difluoromethyl groups are frequently incorporated into pharmaceuticals due to their ability to enhance metabolic stability, improve binding affinity to biological targets, and increase lipophilicity. For instance, studies have shown that compounds containing difluoromethyl groups often exhibit improved pharmacokinetic profiles, making them more suitable for therapeutic applications. The hydroxyl group at the 3-position further adds to the reactivity of the molecule, allowing for various functionalization strategies that can tailor its biological activity.

In the realm of medicinal chemistry, 4,6-Dibromo-2-(difluoromethyl)-3-hydroxypyridine has been explored as a precursor for developing small-molecule inhibitors targeting various disease-related pathways. Recent research has highlighted its potential in the design of kinase inhibitors, which are crucial in treating cancers and inflammatory diseases. The brominated pyridines serve as key motifs in these inhibitors due to their ability to form stable interactions with protein targets. Additionally, the hydroxyl group can be utilized to introduce further modifications that enhance binding specificity.

Agrochemical applications of this compound are also noteworthy. Pyridine derivatives are widely used in pesticides and herbicides due to their efficacy in disrupting enzymatic pathways in pests. The structural features of 4,6-Dibromo-2-(difluoromethyl)-3-hydroxypyridine make it a promising candidate for developing novel agrochemicals that offer improved selectivity and reduced environmental impact. By leveraging its reactivity, researchers can design compounds that target specific pests while minimizing harm to non-target organisms.

The synthesis of 4,6-Dibromo-2-(difluoromethyl)-3-hydroxypyridine typically involves multi-step organic transformations starting from commercially available pyridine precursors. Key steps include halogenation reactions to introduce the bromine atoms at the 4- and 6-positions, followed by functionalization at the 2-position with a difluoromethyl group. The hydroxyl group is often introduced through selective oxidation or hydrolysis of a corresponding methyl or ethyl substituent. These synthetic routes highlight the compound's synthetic utility and its potential for further derivatization.

Recent advancements in catalytic methods have further enhanced the accessibility of 4,6-Dibromo-2-(difluoromethyl)-3-hydroxypyridine. Transition-metal-catalyzed reactions, particularly those involving palladium and copper catalysts, have enabled efficient functionalization of pyridine rings under mild conditions. These methods not only improve yield but also reduce waste, aligning with green chemistry principles. Such innovations have made it feasible to explore more complex derivatives of this compound with greater ease.

The biological activity of 4,6-Dibromo-2-(difluoromethyl)-3-hydroxypyridine has been investigated in various preclinical studies. Initial screenings have revealed promising results in inhibiting certain enzymes associated with infectious diseases and cancer. The bromo and difluoromethyl groups contribute to its binding interactions with these enzymes by forming hydrogen bonds and hydrophobic interactions. Further studies are underway to optimize its potency and selectivity for therapeutic use.

In conclusion,4,6-Dibromo-2-(difluoromethyl)-3-hydroxypyridine (CAS No. 1805042-99-2) is a versatile compound with significant potential in pharmaceutical and agrochemical research. Its unique structural features enable diverse synthetic strategies and biological applications. As research continues to uncover new uses for this molecule,its importance is likely to grow further,contributing to advancements in drug discovery and agricultural science.

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