Cas no 1805578-57-7 (3-Bromo-4-fluoro-5-nitropyridine)

3-Bromo-4-fluoro-5-nitropyridine is a halogenated and nitrated pyridine derivative, serving as a versatile intermediate in pharmaceutical and agrochemical synthesis. Its key structural features—bromo, fluoro, and nitro substituents—enhance reactivity, enabling selective functionalization in cross-coupling reactions, nucleophilic substitutions, and other transformations. The electron-withdrawing nitro group further facilitates electrophilic aromatic substitutions, while the halogen atoms provide sites for metal-catalyzed reactions. This compound is particularly valuable in the development of bioactive molecules due to its ability to introduce multiple functional groups in a single step. High purity and stability under controlled conditions ensure consistent performance in synthetic applications.
3-Bromo-4-fluoro-5-nitropyridine structure
1805578-57-7 structure
Product Name:3-Bromo-4-fluoro-5-nitropyridine
CAS No:1805578-57-7
MF:C5H2BrFN2O2
MW:220.983983516693
CID:4900683
Update Time:2025-11-06

3-Bromo-4-fluoro-5-nitropyridine Chemical and Physical Properties

Names and Identifiers

    • 3-Bromo-4-fluoro-5-nitropyridine
    • [O-][N+](=O)c1cncc(Br)c1F
    • Inchi: 1S/C5H2BrFN2O2/c6-3-1-8-2-4(5(3)7)9(10)11/h1-2H
    • InChI Key: DFHDITMOUQZLKS-UHFFFAOYSA-N
    • SMILES: BrC1=CN=CC(=C1F)[N+](=O)[O-]

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 0
  • Complexity: 163
  • XLogP3: 1.5
  • Topological Polar Surface Area: 58.7

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Additional information on 3-Bromo-4-fluoro-5-nitropyridine

3-Bromo-4-fluoro-5-nitropyridine (CAS No. 1805578-57-7): A Versatile Building Block in Modern Chemistry

3-Bromo-4-fluoro-5-nitropyridine (CAS No. 1805578-57-7) is a highly functionalized pyridine derivative that has gained significant attention in pharmaceutical and agrochemical research. This compound serves as a crucial intermediate in the synthesis of various biologically active molecules, making it an essential building block for medicinal chemists. The presence of multiple substituents - bromo, fluoro, and nitro groups - on the pyridine ring offers unique reactivity patterns that enable diverse chemical transformations.

The molecular structure of 3-bromo-4-fluoro-5-nitropyridine features three distinct functional groups strategically positioned on the aromatic ring. The bromine atom at the 3-position provides an excellent site for cross-coupling reactions, while the fluorine atom at the 4-position enhances the compound's metabolic stability in potential drug candidates. The nitro group at the 5-position serves as both an electron-withdrawing group and a potential precursor for amino functionality through reduction. This combination of features makes CAS 1805578-57-7 particularly valuable in structure-activity relationship studies.

Recent trends in drug discovery have increased demand for fluorinated pyridine derivatives, as evidenced by growing search queries for "fluorine in drug design" and "halogenated heterocycles." The incorporation of fluorine atoms into pharmaceutical compounds has become a hot topic due to their ability to improve metabolic stability, membrane permeability, and binding affinity. 3-Bromo-4-fluoro-5-nitropyridine synthesis methods are frequently searched by researchers looking to incorporate these beneficial properties into their molecules.

In material science applications, nitropyridine compounds like 1805578-57-7 are being explored for their potential in organic electronics. The electron-deficient nature of the nitropyridine moiety makes it interesting for developing n-type organic semiconductors, a rapidly growing field with increasing patent activity. Searches for "nitropyridine electronic applications" have shown steady growth over the past two years, reflecting this emerging interest.

The synthetic utility of 3-bromo-4-fluoro-5-nitropyridine extends to palladium-catalyzed cross-coupling reactions, a topic that consistently ranks high in chemical literature searches. The bromine substituent allows for efficient Suzuki, Stille, or Buchwald-Hartwig couplings, enabling the construction of complex molecular architectures. This reactivity explains why "pyridine cross-coupling reactions" remains one of the most searched terms in organic chemistry databases.

From a commercial perspective, the global market for functionalized pyridine derivatives has been expanding, driven by pharmaceutical industry demand. Market analysis reports indicate particular growth in Asia-Pacific regions, where "pyridine intermediate suppliers" searches have increased by 35% year-over-year. CAS 1805578-57-7 fits perfectly into this market trend as a versatile intermediate with multiple applications.

Environmental and safety considerations for handling 3-bromo-4-fluoro-5-nitropyridine follow standard laboratory protocols for nitrated compounds. While not classified as hazardous under normal handling conditions, proper personal protective equipment is recommended. This safety profile makes it preferable to more reactive intermediates in many synthetic applications, a factor contributing to its growing popularity in research settings.

The compound's stability under various conditions has been the subject of several recent studies, with "nitropyridine stability" appearing frequently in search analytics. Researchers appreciate that 1805578-57-7 maintains integrity under typical storage conditions while remaining reactive enough for diverse transformations. This balance between stability and reactivity makes it particularly valuable for multi-step syntheses.

Future research directions for 3-bromo-4-fluoro-5-nitropyridine derivatives may include exploration in metal-organic frameworks (MOFs) or as ligands in catalytic systems. The increasing number of publications mentioning "pyridine-based MOFs" suggests this could be a promising area of application. The compound's multiple coordination sites make it an attractive candidate for such advanced materials development.

In conclusion, 3-Bromo-4-fluoro-5-nitropyridine (CAS No. 1805578-57-7) represents a strategically important chemical intermediate with wide-ranging applications in medicinal chemistry, materials science, and synthetic methodology development. Its unique combination of substituents provides numerous opportunities for structural elaboration, making it a valuable tool for researchers across multiple disciplines. As interest in halogenated heterocycles and nitroaromatic compounds continues to grow, this compound is well-positioned to remain relevant in cutting-edge chemical research.

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