Cas no 1805945-97-4 (4-Bromo-2-nitropyridin-3-ol)

4-Bromo-2-nitropyridin-3-ol is a brominated and nitrated pyridine derivative with significant utility in synthetic organic chemistry. Its structure, featuring both bromo and nitro substituents on the pyridine ring, makes it a versatile intermediate for nucleophilic aromatic substitution and cross-coupling reactions. The hydroxyl group at the 3-position further enhances its reactivity, enabling functionalization for the synthesis of complex heterocyclic compounds. This compound is particularly valuable in pharmaceutical and agrochemical research, where it serves as a precursor for the development of bioactive molecules. Its well-defined reactivity profile and stability under standard conditions ensure consistent performance in diverse synthetic applications.
4-Bromo-2-nitropyridin-3-ol structure
4-Bromo-2-nitropyridin-3-ol structure
Product Name:4-Bromo-2-nitropyridin-3-ol
CAS No:1805945-97-4
MF:C5H3BrN2O3
MW:218.9929
MDL:MFCD28741191
CID:4741205
PubChem ID:18414212
Update Time:2026-02-25

4-Bromo-2-nitropyridin-3-ol Chemical and Physical Properties

Names and Identifiers

    • 4-Bromo-3-hydroxy-2-nitropyridine
    • 4-Bromo-2-nitropyridin-3-ol
    • EN300-7425819
    • PS-18546
    • 1805945-97-4
    • 4-bromo-2-nitro-3-Pyridinol
    • MFCD28741191
    • starbld0018074
    • CS-0310105
    • 4-bromo-2-nitro-pyridin-3-ol
    • DB-412343
    • D96885
    • SCHEMBL7682478
    • SY274219
    • MDL: MFCD28741191
    • Inchi: 1S/C5H3BrN2O3/c6-3-1-2-7-5(4(3)9)8(10)11/h1-2,9H
    • InChI Key: RWQSFGYTNNNPCN-UHFFFAOYSA-N
    • SMILES: BrC1C([H])=C([H])N=C(C=1O[H])[N+](=O)[O-]

Computed Properties

  • Exact Mass: 217.9327g/mol
  • Monoisotopic Mass: 217.9327g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 160
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Molecular Weight: 218.99g/mol
  • XLogP3: 1.9
  • Topological Polar Surface Area: 78.9

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Additional information on 4-Bromo-2-nitropyridin-3-ol

Professional Introduction to 4-Bromo-2-nitropyridin-3-ol (CAS No. 1805945-97-4)

4-Bromo-2-nitropyridin-3-ol, identified by the Chemical Abstracts Service Number (CAS No.) 1805945-97-4, is a significant intermediate in the realm of pharmaceutical and agrochemical research. This compound belongs to the nitropyridine family, a class of heterocyclic molecules that have garnered considerable attention due to their versatile reactivity and biological potential. The presence of both bromine and nitro substituents on the pyridine ring enhances its utility in synthetic chemistry, making it a valuable building block for the development of novel molecules.

The structural features of 4-Bromo-2-nitropyridin-3-ol contribute to its unique chemical properties. The bromine atom at the 4-position and the nitro group at the 2-position introduce electrophilic centers that are conducive to nucleophilic substitution reactions, while the hydroxyl group at the 3-position provides a site for further functionalization. These attributes have positioned this compound as a key intermediate in the synthesis of more complex structures, particularly in drug discovery efforts targeting various therapeutic areas.

In recent years, there has been a surge in research focused on developing small-molecule inhibitors for protein-protein interactions (PPIs), which play a crucial role in numerous biological pathways. 4-Bromo-2-nitropyridin-3-ol has emerged as a valuable scaffold in this context. Its pyridine core can be modified to interact with specific pockets on target proteins, while the bromine and nitro groups allow for further derivatization to optimize binding affinity and selectivity. For instance, studies have demonstrated its utility in designing inhibitors targeting kinases and transcription factors, which are implicated in cancer and inflammatory diseases.

Moreover, the pharmaceutical industry has shown interest in leveraging 4-Bromo-2-nitropyridin-3-ol for the development of antiviral and antibacterial agents. The nitro group, known for its ability to engage in hydrogen bonding and hydrophobic interactions, can be strategically positioned to disrupt viral protease activity or bacterial metabolic pathways. Recent advancements in medicinal chemistry have highlighted its role in generating lead compounds that exhibit promising antiviral effects against emerging pathogens.

The agrochemical sector has also benefited from the versatility of 4-Bromo-2-nitropyridin-3-ol. Its structural motifs are often incorporated into herbicides and fungicides designed to enhance crop protection. By modifying the substituents on the pyridine ring, researchers can fine-tune the biological activity of these compounds, ensuring efficacy against pests while minimizing environmental impact. This aligns with global efforts to develop sustainable agricultural practices that rely on innovative chemical solutions.

From a synthetic chemistry perspective, 4-Bromo-2-nitropyridin-3-ol serves as a versatile precursor for constructing more complex heterocycles. Its reactivity allows for diverse transformations, including Suzuki-Miyaura cross-coupling, Buchwald-Hartwig amination, and metal-catalyzed reductions. These reactions enable chemists to explore new molecular architectures with potential therapeutic applications. The compound’s ability to undergo multiple functionalizations makes it an indispensable tool in modern synthetic laboratories.

The growing interest in 4-Bromo-2-nitropyridin-3-ol is further underscored by its increasing presence in patent literature and scientific publications. Researchers worldwide are utilizing this compound to explore novel drug candidates, with particular focus on oncology and neurology. The ability to modify its core structure while maintaining key pharmacophoric elements has led to several high-profile discoveries that are currently undergoing preclinical evaluation.

In conclusion, 4-Bromo-2-nitropyridin-3-ol (CAS No. 1805945-97-4) represents a cornerstone in contemporary chemical research, bridging the gap between academic discovery and industrial application. Its unique structural features and reactivity make it an indispensable intermediate for developing innovative solutions across pharmaceuticals, agrochemicals, and materials science. As research continues to evolve, this compound is poised to play an even greater role in shaping the future of chemical innovation.

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