Cas no 1227562-02-8 (2-bromo-5-fluoropyridine-3-carbaldehyde)

2-Bromo-5-fluoropyridine-3-carbaldehyde is a versatile heterocyclic building block widely used in pharmaceutical and agrochemical synthesis. Its key structural features—a bromo substituent at the 2-position and a fluorine at the 5-position—enhance reactivity in cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, facilitating the introduction of diverse functional groups. The aldehyde moiety at the 3-position offers further derivatization potential, enabling condensation or nucleophilic addition reactions. This compound’s high purity and stability make it a reliable intermediate for constructing complex pyridine-based scaffolds. Its utility in medicinal chemistry is underscored by its role in developing bioactive molecules, particularly kinase inhibitors and antimicrobial agents.
2-bromo-5-fluoropyridine-3-carbaldehyde structure
1227562-02-8 structure
Product Name:2-bromo-5-fluoropyridine-3-carbaldehyde
CAS No:1227562-02-8
MF:C6H3BrFNO
MW:203.996524095535
CID:2618129
PubChem ID:72212807
Update Time:2025-08-11

2-bromo-5-fluoropyridine-3-carbaldehyde Chemical and Physical Properties

Names and Identifiers

    • 2-bromo-5-fluoropyridine-3-carbaldehyde
    • F74816
    • XH0817
    • MFCD16606507
    • 1227562-02-8
    • AB70943
    • DB-164116
    • 2-BROMO-5-FLUORONICOTINALDEHYDE
    • SCHEMBL16382668
    • Inchi: 1S/C6H3BrFNO/c7-6-4(3-10)1-5(8)2-9-6/h1-3H
    • InChI Key: SRLHILIBOUSBPT-UHFFFAOYSA-N
    • SMILES: BrC1C(C=O)=CC(=CN=1)F

Computed Properties

  • Exact Mass: 202.93820g/mol
  • Monoisotopic Mass: 202.93820g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 1
  • Complexity: 133
  • 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
  • XLogP3: 1.4
  • Topological Polar Surface Area: 30?2

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Additional information on 2-bromo-5-fluoropyridine-3-carbaldehyde

Professional Introduction to 2-bromo-5-fluoropyridine-3-carbaldehyde (CAS No: 1227562-02-8)

2-bromo-5-fluoropyridine-3-carbaldehyde is a highly versatile and significant compound in the field of chemical and pharmaceutical research. With the CAS number 1227562-02-8, this heterocyclic aldehyde has garnered considerable attention due to its unique structural properties and broad applicability in synthetic chemistry and drug development. This introduction aims to provide a comprehensive overview of the compound, its chemical characteristics, and its emerging role in contemporary scientific research.

The molecular structure of 2-bromo-5-fluoropyridine-3-carbaldehyde consists of a pyridine ring substituted with a bromine atom at the 2-position, a fluorine atom at the 5-position, and an aldehyde group at the 3-position. This specific arrangement of functional groups makes it an invaluable intermediate in organic synthesis, particularly in the construction of more complex molecules. The presence of both bromine and fluorine atoms enhances its reactivity, allowing for diverse chemical transformations such as cross-coupling reactions, nucleophilic substitutions, and condensation reactions.

In recent years, 2-bromo-5-fluoropyridine-3-carbaldehyde has found extensive use in the development of pharmaceuticals. Its pyridine core is a common motif in many bioactive molecules, and the aldehyde functionality provides a reactive site for further derivatization. One of the most notable applications is in the synthesis of kinase inhibitors, which are crucial in treating various types of cancer and inflammatory diseases. The bromo and fluoro substituents not only improve the metabolic stability of these inhibitors but also enhance their binding affinity to target proteins.

Moreover, this compound has been explored in the field of medicinal chemistry for its potential as a building block in the creation of novel therapeutic agents. Researchers have leveraged its reactivity to develop new analogs with improved pharmacological properties. For instance, studies have shown that derivatives of 2-bromo-5-fluoropyridine-3-carbaldehyde exhibit significant activity against enzymes involved in bacterial resistance mechanisms. This underscores its importance in combating antibiotic-resistant pathogens, a growing concern in global healthcare.

The synthesis of 2-bromo-5-fluoropyridine-3-carbaldehyde typically involves multi-step organic reactions starting from commercially available pyridine precursors. The introduction of bromine and fluorine atoms is achieved through well-established halogenation techniques, while the aldehyde group is introduced via oxidation or formylation reactions. These synthetic pathways highlight the compound's accessibility and utility for researchers working in both academic and industrial settings.

The role of computational chemistry has also been instrumental in understanding the reactivity and potential applications of 2-bromo-5-fluoropyridine-3-carbaldehyde. Advanced molecular modeling techniques have enabled researchers to predict how this compound interacts with biological targets, providing insights into its mechanism of action. This computational approach complements experimental studies, leading to more efficient drug discovery processes.

In conclusion, 2-bromo-5-fluoropyridine-3-carbaldehyde (CAS No: 1227562-02-8) is a pivotal compound in modern chemical research. Its unique structural features make it an excellent intermediate for synthesizing complex molecules, particularly in pharmaceutical applications. As research continues to uncover new therapeutic possibilities, this compound will undoubtedly remain at the forefront of scientific innovation.

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