Cas no 102249-56-9 (2-bromo-5-phenylpyridin-3-amine)

2-bromo-5-phenylpyridin-3-amine structure
102249-56-9 structure
Product Name:2-bromo-5-phenylpyridin-3-amine
CAS No:102249-56-9
MF:C11H9BrN2
MW:249.106561422348
CID:1093185
PubChem ID:13495914
Update Time:2025-07-18

2-bromo-5-phenylpyridin-3-amine Chemical and Physical Properties

Names and Identifiers

    • 2-bromo-5-phenylpyridin-3-amine
    • 102249-56-9
    • Inchi: 1S/C11H9BrN2/c12-11-10(13)6-9(7-14-11)8-4-2-1-3-5-8/h1-7H,13H2
    • InChI Key: AYGHOJDCYZEXGX-UHFFFAOYSA-N
    • SMILES: BrC1=C(C=C(C=N1)C1C=CC=CC=1)N

Computed Properties

  • Exact Mass: 247.99491g/mol
  • Monoisotopic Mass: 247.99491g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 14
  • Rotatable Bond Count: 1
  • Complexity: 180
  • 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: 2.8
  • Topological Polar Surface Area: 38.9?2

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Additional information on 2-bromo-5-phenylpyridin-3-amine

Professional Introduction to 2-bromo-5-phenylpyridin-3-amine (CAS No. 102249-56-9)

2-bromo-5-phenylpyridin-3-amine, with the chemical formula C?H?BrN?, is a significant compound in the field of pharmaceutical and agrochemical research. This heterocyclic amine derivative has garnered considerable attention due to its versatile structural framework, which makes it a valuable intermediate in the synthesis of various biologically active molecules. The compound's unique combination of a bromine substituent and a phenyl group on a pyridine core provides multiple sites for further functionalization, enabling the development of novel pharmacophores.

The importance of 2-bromo-5-phenylpyridin-3-amine in modern medicinal chemistry stems from its role as a key building block in the synthesis of small-molecule inhibitors targeting various therapeutic pathways. Recent advancements in drug discovery have highlighted its utility in developing compounds with potential applications in oncology, neurology, and infectious diseases. The bromine atom, in particular, serves as an excellent handle for cross-coupling reactions such as Suzuki-Miyaura and Buchwald-Hartwig couplings, facilitating the introduction of aryl or amino groups at strategic positions within the molecule.

One of the most compelling aspects of 2-bromo-5-phenylpyridin-3-amine is its incorporation into kinase inhibitors, which are critical for treating cancers and inflammatory disorders. The pyridine scaffold is a common motif in many approved drugs due to its ability to interact favorably with biological targets. For instance, studies have demonstrated that derivatives of this compound can modulate the activity of tyrosine kinases by binding to their ATP-binding pockets. The phenyl ring enhances hydrophobic interactions with the target protein, while the amine group can form hydrogen bonds, contributing to high affinity and selectivity.

In addition to its role in oncology, 2-bromo-5-phenylpyridin-3-amine has shown promise in the development of antiviral agents. The structural features of this compound allow it to interfere with viral replication by inhibiting essential enzymes or disrupting protein-protein interactions. Researchers have explored its derivatives as potential inhibitors of viral proteases and polymerases, highlighting its broad applicability in antiviral drug design. The bromine substituent is particularly useful for further derivatization, enabling the creation of libraries of compounds for high-throughput screening.

The agrochemical sector has also benefited from the versatility of 2-bromo-5-phenylpyridin-3-amine. Its structural motif is found in several herbicides and fungicides that target specific enzymes involved in plant growth regulation or pathogen metabolism. By modifying the substituents on the pyridine ring, chemists can fine-tune the biological activity of these compounds to achieve desired effects while minimizing environmental impact. This adaptability makes it an indispensable tool for developing sustainable agricultural solutions.

The synthetic methodologies for preparing 2-bromo-5-phenylpyridin-3-am ine have been refined over recent years, leading to more efficient and scalable processes. Traditional approaches often involve palladium-catalyzed cross-coupling reactions between halogenated pyridines and phenylboronic acids or amines. However, newer techniques employing transition-metal catalysts under milder conditions have improved yields and reduced byproduct formation. These advancements have made it easier for researchers to access this compound and its derivatives for further study.

The pharmacokinetic properties of derivatives of 2-bromo-5-phenylpyridin -3-am ine are another area of active investigation. Understanding how these compounds are absorbed, distributed, metabolized, and excreted (ADME) is crucial for optimizing their therapeutic potential. Computational modeling and experimental studies have revealed that modifications to the pyridine core can significantly influence bioavailability and metabolic stability. This knowledge is essential for designing drugs that exhibit favorable pharmacokinetic profiles.

In conclusion, 2-bromo -5-ph enylpy ridin -3-am ine (CAS No. 102249 -56 -9) represents a cornerstone in modern medicinal chemistry due to its structural versatility and functional diversity. Its applications span across multiple therapeutic areas, from oncology to agrochemistry, underscoring its importance as a synthetic intermediate. As research continues to uncover new ways to utilize this compound and its derivatives, its significance in drug discovery is likely to grow even further.

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