Cas no 944956-08-5 (3-Bromo-4-phenyl-1H-pyrrolo[2,3-b]pyridine)

3-Bromo-4-phenyl-1H-pyrrolo[2,3-b]pyridine is a heterocyclic compound featuring a fused pyrrolopyridine core substituted with a bromine atom at the 3-position and a phenyl group at the 4-position. This structure serves as a versatile intermediate in medicinal chemistry and materials science, particularly in the synthesis of biologically active molecules and functional materials. The bromine substituent enhances reactivity for further functionalization via cross-coupling reactions, while the phenyl group contributes to π-stacking interactions, influencing molecular properties. Its well-defined scaffold is valuable for designing inhibitors, ligands, and optoelectronic materials. The compound is typically characterized by high purity and stability, ensuring reliable performance in synthetic applications.
3-Bromo-4-phenyl-1H-pyrrolo[2,3-b]pyridine structure
944956-08-5 structure
Product Name:3-Bromo-4-phenyl-1H-pyrrolo[2,3-b]pyridine
CAS No:944956-08-5
MF:C13H9BrN2
MW:273.127961874008
CID:4927344
Update Time:2025-10-28

3-Bromo-4-phenyl-1H-pyrrolo[2,3-b]pyridine Chemical and Physical Properties

Names and Identifiers

    • 3-bromo-4-phenyl-1H-pyrrolo[2,3-b]pyridine
    • 3-Bromo-4-phenyl-1H-pyrrolo[2,3-b]pyridine
    • Inchi: 1S/C13H9BrN2/c14-11-8-16-13-12(11)10(6-7-15-13)9-4-2-1-3-5-9/h1-8H,(H,15,16)
    • InChI Key: IQIMIVGEUAMPKB-UHFFFAOYSA-N
    • SMILES: BrC1=CNC2C1=C(C=CN=2)C1C=CC=CC=1

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 1
  • Complexity: 240
  • XLogP3: 3.6
  • Topological Polar Surface Area: 28.7

3-Bromo-4-phenyl-1H-pyrrolo[2,3-b]pyridine Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
Alichem
A023023166-250mg
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Alichem
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Additional information on 3-Bromo-4-phenyl-1H-pyrrolo[2,3-b]pyridine

Professional Introduction to 3-Bromo-4-phenyl-1H-pyrrolo[2,3-b]pyridine (CAS No. 944956-08-5)

3-Bromo-4-phenyl-1H-pyrrolo[2,3-b]pyridine, with the chemical formula C??H?BrN?, is a heterocyclic compound that has garnered significant attention in the field of pharmaceutical research and drug development. This compound belongs to the class of pyrrolopyridines, which are known for their diverse biological activities and potential applications in medicinal chemistry. The presence of both bromine and phenyl substituents makes it a valuable intermediate in the synthesis of more complex molecules, particularly in the exploration of novel therapeutic agents.

The< strong>CAS number 944956-08-5 uniquely identifies this compound and distinguishes it from other isomers or analogs. Its molecular structure consists of a fused pyrrole and pyridine ring system, which is a common motif in bioactive molecules. The bromine atom at the 3-position and the phenyl group at the 4-position contribute to its reactivity and make it a versatile building block for further chemical modifications.

In recent years, there has been a growing interest in< strong>pyrrolopyridine derivatives due to their demonstrated efficacy in various pharmacological contexts. These compounds have shown promise as inhibitors of kinases, enzymes involved in signal transduction pathways, and other targets relevant to cancer and inflammatory diseases. The< strong>3-Bromo-4-phenyl-1H-pyrrolo[2,3-b]pyridine structure provides a scaffold that can be modified to enhance binding affinity and selectivity for specific biological targets.

One of the most compelling aspects of this compound is its utility in the synthesis of small-molecule inhibitors. Researchers have leveraged its< strong>brominated aromatic ring to introduce further functional groups through cross-coupling reactions such as Suzuki-Miyaura or Buchwald-Hartwig couplings. These reactions allow for the precise attachment of pharmacophores that can modulate biological activity. For instance, studies have demonstrated that derivatives of< strong>3-Bromo-4-phenyl-1H-pyrrolo[2,3-b]pyridine can exhibit inhibitory effects on protein kinases, which are critical targets in oncology research.

The< strong>phenyl substituent at the 4-position of the pyrrolopyridine core contributes to the compound's overall physicochemical properties, including solubility and metabolic stability. This feature is particularly important in drug design, as it can influence how a molecule behaves within an organism. Additionally, the bromine atom provides a handle for further chemical manipulation, enabling researchers to explore a wide range of structural variations.

Recent advances in computational chemistry have further enhanced the understanding of how< strong>3-Bromo-4-phenyl-1H-pyrrolo[2,3-b]pyridine interacts with biological targets. Molecular docking studies have been instrumental in predicting binding modes and identifying key residues involved in receptor recognition. These insights have guided the optimization of lead compounds toward improved potency and reduced off-target effects. The integration of experimental data with computational modeling has become a cornerstone of modern drug discovery strategies.

In clinical research, derivatives of this compound have been investigated for their potential therapeutic applications. Preclinical studies have shown that certain analogs exhibit anti-proliferative properties by inhibiting key signaling pathways implicated in cancer progression. The< strong>bromophenyl moiety appears to play a crucial role in mediating these effects by interacting with specific amino acid residues in target proteins. Such findings underscore the importance of< strong>CAS No. 944956-08-5-derived compounds as candidates for further development into novel therapeutics.

The synthesis of< strong>3-Bromo-4-phenyl-1H-pyrrolo[2,3-b]pyridine itself presents an interesting challenge due to its complex heterocyclic framework. Traditional synthetic routes often involve multi-step sequences that require careful control over reaction conditions to achieve high yields and purity. However, recent methodologies have emerged that streamline these processes, making it more feasible to produce this compound on a larger scale for research purposes.

The pharmaceutical industry continues to invest heavily in exploring novel heterocyclic scaffolds like< strong>pyrrolopyridines. The versatility of< strong>CAS No. 944956-08-5-based compounds makes them attractive for designing molecules with tailored biological activities. As our understanding of disease mechanisms evolves, so too does our ability to rationally design molecules that can modulate these pathways effectively.

In conclusion,< strong>3-Bromo-4-phenyl-1H-pyrrolo[2,3-b]pyridine represents a significant advancement in pharmaceutical chemistry due to its structural features and potential applications. Its unique combination of substituents—particularly the bromo and phenyl groups—makes it a valuable intermediate for synthesizing bioactive molecules. Ongoing research continues to uncover new ways this compound can be utilized in drug development efforts aimed at addressing some of medicine's most pressing challenges.

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