Cas no 1060809-69-9 (4-Amino-6-bromo-pyridine-3-carbaldehyde)

4-Amino-6-bromo-pyridine-3-carbaldehyde is a versatile heterocyclic compound featuring both amino and bromo functional groups, along with an aldehyde moiety. Its structure makes it a valuable intermediate in organic synthesis, particularly for the preparation of pharmaceuticals, agrochemicals, and functional materials. The presence of reactive sites allows for selective modifications, enabling the construction of complex molecular frameworks. The bromo substituent facilitates cross-coupling reactions, while the aldehyde group serves as a key handle for condensation or nucleophilic addition reactions. This compound is commonly employed in medicinal chemistry for the development of bioactive molecules due to its ability to act as a building block for nitrogen-containing heterocycles.
4-Amino-6-bromo-pyridine-3-carbaldehyde structure
1060809-69-9 structure
Product Name:4-Amino-6-bromo-pyridine-3-carbaldehyde
CAS No:1060809-69-9
MF:C6H5BrN2O
MW:201.020700216293
MDL:MFCD13189280
CID:1171265
PubChem ID:72212268
Update Time:2025-10-29

4-Amino-6-bromo-pyridine-3-carbaldehyde Chemical and Physical Properties

Names and Identifiers

    • 4-amino-6-bromopyridine-3-carbaldehyde
    • 4-Amino-6-bromo-pyridine-3-carbaldehyde
    • 4-AMINO-6-BROMONICOTINALDEHYDE
    • 1060809-69-9
    • DB-184744
    • DRJIKOFVEUVPSW-UHFFFAOYSA-N
    • MFCD13189280
    • AT27141
    • CS-0158796
    • SCHEMBL15873128
    • AB68108
    • MDL: MFCD13189280
    • Inchi: 1S/C6H5BrN2O/c7-6-1-5(8)4(3-10)2-9-6/h1-3H,(H2,8,9)
    • InChI Key: DRJIKOFVEUVPSW-UHFFFAOYSA-N
    • SMILES: BrC1=CC(=C(C=O)C=N1)N

Computed Properties

  • Exact Mass: 199.95853g/mol
  • Monoisotopic Mass: 199.95853g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 1
  • Complexity: 131
  • 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: 1.2
  • Topological Polar Surface Area: 56?2

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Additional information on 4-Amino-6-bromo-pyridine-3-carbaldehyde

Introduction to 4-Amino-6-bromo-pyridine-3-carbaldehyde (CAS No. 1060809-69-9)

4-Amino-6-bromo-pyridine-3-carbaldehyde, identified by the Chemical Abstracts Service (CAS) number 1060809-69-9, is a versatile heterocyclic compound that has garnered significant attention in the field of pharmaceutical and chemical research. This compound belongs to the pyridine family, a class of nitrogen-containing heterocycles that are widely recognized for their diverse biological activities and industrial applications. The presence of both amino and aldehyde functional groups, coupled with a bromine substituent, makes 4-amino-6-bromo-pyridine-3-carbaldehyde a valuable intermediate in synthetic chemistry, particularly in the development of novel therapeutic agents.

The structural features of 4-amino-6-bromo-pyridine-3-carbaldehyde contribute to its reactivity and utility in multiple synthetic pathways. The amino group at the 4-position and the aldehyde group at the 3-position provide opportunities for further functionalization, enabling the construction of more complex molecular architectures. Additionally, the bromine atom at the 6-position serves as a handle for cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig couplings, which are pivotal in modern drug discovery.

In recent years, there has been a surge in research focused on developing small-molecule inhibitors targeting various disease pathways. 4-Amino-6-bromo-pyridine-3-carbaldehyde has emerged as a key building block in the synthesis of inhibitors for enzymes involved in cancer metabolism, inflammation, and infectious diseases. For instance, studies have demonstrated its role in generating derivatives that exhibit potent activity against kinases and other enzymes implicated in aberrant signaling pathways.

One of the most compelling applications of 4-amino-6-bromo-pyridine-3-carbaldehyde is in the development of antiviral agents. The pyridine core is a common motif in many approved antiviral drugs due to its ability to interact with viral proteases and polymerases. Researchers have leveraged this compound to design inhibitors targeting viral enzymes such as protease and helicase, which are critical for viral replication. The introduction of halogen atoms into the pyridine ring enhances binding affinity and selectivity, making these derivatives more effective against viral targets.

The bromine substituent in 4-amino-6-bromo-pyridine-3-carbaldehyde also facilitates its use in fragment-based drug design strategies. By serving as a point of attachment for pharmacophores, this compound enables the rapid assembly of libraries of drug-like molecules. Fragment-based approaches have gained prominence in recent years due to their efficiency in identifying novel lead compounds with high binding affinity to biological targets.

Advances in computational chemistry have further enhanced the utility of 4-amino-6-bromo-pyridine-3-carbaldehyde as a scaffold for drug discovery. Molecular docking simulations and virtual screening techniques have been employed to predict binding interactions between this compound and target proteins. These computational methods have accelerated the identification of promising candidates for further optimization, reducing the time and cost associated with traditional high-throughput screening.

The synthesis of 4-amino-6-bromo-pyridine-3-carbaldehyde itself is an area of active interest. Researchers have developed efficient synthetic routes that maximize yield while minimizing byproducts. These methods often involve multi-step transformations starting from readily available precursors, such as bromopyridines or aminoaldehydes. The optimization of synthetic protocols ensures that sufficient quantities of this compound are available for preclinical and clinical studies.

In conclusion, 4-amino-6-bromo-pyridine-3-carbaldehyde (CAS No. 1060809-69-9) represents a significant advancement in medicinal chemistry due to its structural versatility and functional reactivity. Its role as an intermediate in synthesizing bioactive molecules has positioned it as a cornerstone in drug discovery efforts targeting various diseases. As research continues to uncover new therapeutic applications, this compound is poised to remain at the forefront of pharmaceutical innovation.

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