Cas no 1227588-59-1 (6-bromo-5-fluoronicotinaldehyde)

6-Bromo-5-fluoronicotinaldehyde is a versatile heteroaromatic aldehyde used as a key intermediate in organic synthesis and pharmaceutical research. Its structure, featuring both bromo and fluoro substituents on the pyridine ring, enhances reactivity in cross-coupling reactions, nucleophilic substitutions, and other functionalization processes. The aldehyde group provides a handle for further derivatization, enabling the synthesis of complex molecules. This compound is particularly valuable in medicinal chemistry for the development of bioactive compounds due to its ability to modulate electronic and steric properties. High purity and consistent quality ensure reliable performance in demanding applications. Its stability under standard conditions makes it a practical choice for laboratory and industrial use.
6-bromo-5-fluoronicotinaldehyde structure
1227588-59-1 structure
Product Name:6-bromo-5-fluoronicotinaldehyde
CAS No:1227588-59-1
MF:C6H3BrFNO
MW:203.996524095535
MDL:MFCD16606505
CID:2125402
PubChem ID:72212806
Update Time:2025-05-20

6-bromo-5-fluoronicotinaldehyde Chemical and Physical Properties

Names and Identifiers

    • 6-bromo-5-fluoronicotinaldehyde
    • 6-Bromo-5-fluoro-pyridine-3-carbaldehyde
    • 6-bromo-5-fluoropyridine-3-carbaldehyde
    • DB-341733
    • DS-19559
    • SCHEMBL359521
    • AB70942
    • CS-0187189
    • EN300-7655006
    • SY269550
    • MFCD16606505
    • AKOS030528629
    • 1227588-59-1
    • O11553
    • MDL: MFCD16606505
    • Inchi: 1S/C6H3BrFNO/c7-6-5(8)1-4(3-10)2-9-6/h1-3H
    • InChI Key: MIVNLXDUQDPXJR-UHFFFAOYSA-N
    • SMILES: BrC1=C(C=C(C=O)C=N1)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 6-bromo-5-fluoronicotinaldehyde

Introduction to 6-bromo-5-fluoronicotinaldehyde (CAS No: 1227588-59-1)

6-bromo-5-fluoronicotinaldehyde, with the chemical identifier CAS No: 1227588-59-1, is a specialized organic compound that has garnered significant attention in the field of pharmaceutical and medicinal chemistry. This compound belongs to the class of nicotinaldehyde derivatives, characterized by the presence of both bromine and fluorine substituents on the pyridine ring. The strategic positioning of these halogen atoms imparts unique electronic and steric properties, making it a valuable intermediate in the synthesis of biologically active molecules.

The structural motif of 6-bromo-5-fluoronicotinaldehyde is particularly intriguing due to its potential as a building block for drug discovery. The bromine atom at the 6-position and the fluorine atom at the 5-position create a versatile platform for further functionalization, enabling chemists to explore diverse chemical spaces. This compound has been increasingly utilized in the development of novel therapeutic agents, where its reactivity and stability under various conditions make it an attractive choice.

In recent years, there has been a surge in research focused on halogenated pyridines as pharmacophores. These compounds have shown promise in modulating various biological pathways, including enzyme inhibition and receptor binding. The presence of both bromine and fluorine in 6-bromo-5-fluoronicotinaldehyde enhances its potential as a scaffold for designing molecules with improved pharmacokinetic properties. For instance, fluorine substitution is known to enhance metabolic stability, while bromine can serve as a handle for further derivatization via cross-coupling reactions.

One of the most notable applications of 6-bromo-5-fluoronicotinaldehyde is in the synthesis of kinase inhibitors. Kinases are enzymes that play a crucial role in many cellular processes, and their dysregulation is often associated with diseases such as cancer. By leveraging the reactivity of this compound, researchers have been able to develop potent inhibitors that target specific kinases. The bromine atom allows for palladium-catalyzed cross-coupling reactions, such as Suzuki or Buchwald-Hartwig couplings, which are essential for constructing complex molecular architectures.

Moreover, the fluorine atom in 6-bromo-5-fluoronicotinaldehyde contributes to the compound's binding affinity by participating in hydrogen bonding interactions with biological targets. This feature has been exploited in the design of ligands that exhibit high selectivity for certain proteins. For example, recent studies have demonstrated its utility in generating inhibitors of protein-protein interactions, which are challenging to target with traditional small-molecule drugs.

The synthesis of 6-bromo-5-fluoronicotinaldehyde typically involves multi-step organic transformations starting from commercially available precursors. The introduction of bromine and fluorine substituents requires careful selection of reagents and conditions to ensure high yield and purity. Advanced synthetic techniques, such as transition metal catalysis and flow chemistry, have been employed to optimize these processes. These methods not only improve efficiency but also minimize waste, aligning with the growing emphasis on sustainable chemistry.

Recent advancements in computational chemistry have further enhanced the utility of 6-bromo-5-fluoronicotinaldehyde as a drug discovery tool. Molecular modeling studies have been conducted to predict how this compound interacts with biological targets at the atomic level. These insights have guided medicinal chemists in designing derivatives with enhanced potency and selectivity. Additionally, virtual screening techniques have been used to identify novel scaffolds based on the structure of this compound, accelerating the drug development pipeline.

The versatility of 6-bromo-5-fluoronicotinaldehyde extends beyond kinase inhibitors. It has also been explored as a precursor for developing antiviral and antibacterial agents. The halogenated pyridine core is known to disrupt viral replication mechanisms and bacterial cell wall synthesis. By incorporating this compound into drug candidates, researchers aim to overcome existing challenges related to drug resistance and efficacy.

In conclusion, 6-bromo-5-fluoronicotinaldehyde (CAS No: 1227588-59-1) represents a significant advancement in medicinal chemistry due to its unique structural features and broad applicability. Its role as an intermediate in synthesizing biologically active molecules underscores its importance in drug discovery efforts. As research continues to uncover new therapeutic applications, this compound is poised to remain at the forefront of innovation in pharmaceutical sciences.

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