Cas no 1227588-66-0 (3-Bromo-2-fluoropyridine-4-carbaldehyde)

3-Bromo-2-fluoropyridine-4-carbaldehyde is a versatile heterocyclic building block widely used in pharmaceutical and agrochemical synthesis. Its key structural features—a bromo and fluoro substituent adjacent to an aldehyde group on the pyridine ring—enable selective functionalization, making it valuable for cross-coupling reactions, nucleophilic substitutions, and further derivatization. The electron-withdrawing effects of the halogen substituents enhance reactivity, particularly in metal-catalyzed transformations. This compound is particularly useful in the development of bioactive molecules, offering precise control over molecular architecture. Its high purity and stability under standard conditions ensure reliable performance in complex synthetic pathways.
3-Bromo-2-fluoropyridine-4-carbaldehyde structure
1227588-66-0 structure
Product Name:3-Bromo-2-fluoropyridine-4-carbaldehyde
CAS No:1227588-66-0
MF:C6H3BrFNO
MW:203.9965
MDL:MFCD16606509
CID:4738408
Update Time:2025-06-15

3-Bromo-2-fluoropyridine-4-carbaldehyde Chemical and Physical Properties

Names and Identifiers

    • 3-bromo-2-fluoroisonicotinaldehyde
    • 3-Bromo-2-fluoropyridine-4-carbaldehyde
    • MDL: MFCD16606509
    • Inchi: 1S/C6H3BrFNO/c7-5-4(3-10)1-2-9-6(5)8/h1-3H
    • InChI Key: BGHGWLSGUBXJMI-UHFFFAOYSA-N
    • SMILES: BrC1C(=NC([H])=C([H])C=1C([H])=O)F

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 1
  • Complexity: 133
  • Topological Polar Surface Area: 30

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Additional information on 3-Bromo-2-fluoropyridine-4-carbaldehyde

Professional Introduction to 3-Bromo-2-fluoropyridine-4-carbaldehyde (CAS No: 1227588-66-0)

3-Bromo-2-fluoropyridine-4-carbaldehyde is a highly significant compound in the field of pharmaceutical chemistry and medicinal biology. This heterocyclic aldehyde, characterized by its unique structural features, has garnered considerable attention due to its versatile applications in the synthesis of biologically active molecules. The compound's molecular structure, featuring both bromine and fluorine substituents, makes it a valuable intermediate in the development of various therapeutic agents.

The chemical properties of 3-Bromo-2-fluoropyridine-4-carbaldehyde are primarily influenced by its aromatic pyridine core and the presence of functional groups such as the aldehyde and halogen atoms. The bromine atom at the 3-position and the fluorine atom at the 2-position introduce electrophilic and electron-withdrawing effects, respectively, which can modulate the reactivity and binding affinity of the molecule. These features make it an excellent candidate for further functionalization, enabling the synthesis of complex derivatives with tailored pharmacological properties.

In recent years, 3-Bromo-2-fluoropyridine-4-carbaldehyde has been extensively studied for its potential in drug discovery. Its structural motif is frequently found in a wide range of bioactive compounds, including kinase inhibitors, antiviral agents, and anti-inflammatory drugs. The aldehyde group serves as a versatile handle for further chemical transformations, such as condensation reactions with amines to form Schiff bases or oxidation to yield carboxylic acids. These transformations are crucial for generating novel scaffolds that can interact with biological targets in unique ways.

One of the most compelling aspects of 3-Bromo-2-fluoropyridine-4-carbaldehyde is its role in the development of small-molecule inhibitors targeting protein-protein interactions. Protein-protein interactions are critical in many biological pathways, making them attractive therapeutic targets. However, designing small molecules that selectively modulate these interactions can be challenging due to the often subtle differences in binding affinities between related proteins. The presence of both bromine and fluorine atoms in 3-Bromo-2-fluoropyridine-4-carbaldehyde allows for precise tuning of electronic properties, which can enhance binding selectivity and potency.

Recent advancements in computational chemistry have further highlighted the utility of 3-Bromo-2-fluoropyridine-4-carbaldehyde as a building block. Molecular modeling studies have demonstrated that subtle modifications to its structure can significantly impact its binding mode to biological targets. For instance, computational analyses have shown that introducing additional substituents at specific positions can enhance interactions with key amino acid residues in protein binding pockets. These insights have guided the design of more effective inhibitors with improved pharmacokinetic profiles.

The synthesis of 3-Bromo-2-fluoropyridine-4-carbaldehyde itself is another area of active research. Efficient synthetic routes are essential for large-scale production and cost-effective drug development. Modern synthetic methodologies often leverage transition metal catalysis to achieve high yields and selectivity. For example, palladium-catalyzed cross-coupling reactions have been employed to introduce bromine and fluorine atoms into the pyridine core with remarkable efficiency. These advances have not only streamlined the synthesis but also opened up new possibilities for structural diversification.

In addition to its applications in drug discovery, 3-Bromo-2-fluoropyridine-4-carbaldehyde has found utility in materials science and agrochemical research. Its unique electronic properties make it a promising candidate for developing organic semiconductors and light-emitting diodes (LEDs). Furthermore, its structural framework can be modified to create novel pesticides with enhanced efficacy and reduced environmental impact.

The growing interest in green chemistry has also influenced the use of 3-Bromo-2-fluoropyridine-4-carbaldehyde. Researchers are increasingly focusing on sustainable synthetic methods that minimize waste and reduce energy consumption. For instance, solvent-free reactions and catalytic processes have been explored as alternatives to traditional wet chemistry approaches. These efforts align with global initiatives to promote environmentally responsible chemical manufacturing.

The future prospects for 3-Bromo-2-fluoropyridine-4-carbaldehyde are promising, with ongoing research expected to uncover new applications and refine existing synthetic strategies. As our understanding of biological systems continues to evolve, so too will our ability to design molecules that interact selectively with disease-causing targets. The compound's versatility makes it a cornerstone in modern medicinal chemistry, driving innovation across multiple therapeutic areas.

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