Cas no 1805103-19-8 (2-Bromo-5-(bromomethyl)-3-methylpyridine)

2-Bromo-5-(bromomethyl)-3-methylpyridine is a brominated pyridine derivative commonly used as an intermediate in organic synthesis and pharmaceutical research. Its key structural features—a bromomethyl group at the 5-position and a bromo substituent at the 2-position—make it a versatile building block for further functionalization, particularly in cross-coupling reactions and nucleophilic substitutions. The presence of two reactive bromine sites allows for selective modifications, enabling the synthesis of complex heterocyclic compounds. This compound is valued for its stability under standard handling conditions and its compatibility with a range of reaction conditions. It is typically employed in the development of agrochemicals, pharmaceuticals, and specialty chemicals requiring precise pyridine-based frameworks.
2-Bromo-5-(bromomethyl)-3-methylpyridine structure
1805103-19-8 structure
Product Name:2-Bromo-5-(bromomethyl)-3-methylpyridine
CAS No:1805103-19-8
MF:C7H7Br2N
MW:264.945180177689
MDL:MFCD28135021
CID:4900097
PubChem ID:54237142
Update Time:2025-05-20

2-Bromo-5-(bromomethyl)-3-methylpyridine Chemical and Physical Properties

Names and Identifiers

    • 2-bromo-5-(bromomethyl)-3-methylpyridine
    • 2-Bromo-5-bromomethyl-3-methylpyridine
    • 2-Bromo-5-(bromomethyl)-3-methylpyridine
    • MDL: MFCD28135021
    • Inchi: 1S/C7H7Br2N/c1-5-2-6(3-8)4-10-7(5)9/h2,4H,3H2,1H3
    • InChI Key: QNJCTOIWAUZOJQ-UHFFFAOYSA-N
    • SMILES: BrCC1C=NC(=C(C)C=1)Br

Computed Properties

  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 1
  • Complexity: 108
  • XLogP3: 2.8
  • Topological Polar Surface Area: 12.9

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Additional information on 2-Bromo-5-(bromomethyl)-3-methylpyridine

Comprehensive Overview of 2-Bromo-5-(bromomethyl)-3-methylpyridine (CAS No. 1805103-19-8)

2-Bromo-5-(bromomethyl)-3-methylpyridine (CAS No. 1805103-19-8) is a highly versatile brominated pyridine derivative that has garnered significant attention in pharmaceutical and agrochemical research. This compound, characterized by its unique molecular structure featuring both bromomethyl and methyl substituents, serves as a critical intermediate in the synthesis of complex organic molecules. Its pyridine backbone, combined with strategic halogenation, makes it a valuable building block for drug discovery and material science applications.

In recent years, the demand for brominated pyridine derivatives like 2-Bromo-5-(bromomethyl)-3-methylpyridine has surged due to their role in developing small-molecule inhibitors and biologically active compounds. Researchers are particularly interested in its potential applications in kinase inhibitor synthesis, a hot topic in oncology and autoimmune disease research. The compound's dual bromine functionality allows for selective cross-coupling reactions, enabling the creation of diverse molecular architectures with high precision.

From a synthetic chemistry perspective, CAS No. 1805103-19-8 offers exceptional reactivity in palladium-catalyzed couplings, such as Suzuki-Miyaura and Buchwald-Hartwig reactions. This aligns with the growing trend toward green chemistry, as these methods often reduce waste and improve atom economy. The compound's stability under various reaction conditions also makes it a preferred choice for high-throughput screening libraries, addressing the pharmaceutical industry's need for efficient lead optimization.

Beyond pharmaceuticals, 2-Bromo-5-(bromomethyl)-3-methylpyridine has shown promise in agrochemical innovation. Its structural motifs are being explored for designing next-generation crop protection agents, particularly in addressing resistance issues in pest management. The methylpyridine core contributes to enhanced bioavailability, a key consideration in modern pesticide development.

Analytical studies of this compound highlight its compatibility with advanced chromatographic techniques, including HPLC and LC-MS, which are essential for quality control in industrial-scale production. The rise of continuous flow chemistry has further amplified interest in such brominated intermediates, as they enable safer handling and improved scalability compared to traditional batch processes.

As the scientific community continues to explore structure-activity relationships (SAR) in medicinal chemistry, 2-Bromo-5-(bromomethyl)-3-methylpyridine remains at the forefront due to its balanced lipophilicity and steric properties. Its molecular weight (265.94 g/mol) and logP value make it particularly suitable for CNS-targeting drug candidates, a rapidly growing segment in neuropharmacology research.

Environmental considerations surrounding brominated compounds have led to increased scrutiny of their ecological impact. However, 1805103-19-8 demonstrates favorable biodegradation profiles in preliminary studies, positioning it as a more sustainable option compared to persistent halogenated analogs. This aspect resonates with current industry priorities for eco-friendly chemical solutions.

The compound's crystalline form and well-defined melting point (reported between 85-88°C) facilitate purification processes, addressing common challenges in high-purity intermediate production. These characteristics are particularly valuable for GMP-compliant synthesis in regulated industries, where consistency and reproducibility are paramount.

Emerging applications in material science have revealed that 2-Bromo-5-(bromomethyl)-3-methylpyridine can serve as a precursor for functionalized polymers with tailored electronic properties. This expands its relevance beyond life sciences into areas like organic electronics and conductive materials, demonstrating the compound's multidisciplinary utility.

In conclusion, CAS No. 1805103-19-8 represents a strategically important chemical entity that bridges multiple scientific domains. Its unique combination of reactivity, stability, and structural versatility ensures its continued relevance in cutting-edge research and industrial applications. As synthetic methodologies evolve and new therapeutic targets emerge, this brominated pyridine derivative will undoubtedly play a pivotal role in shaping future innovations across chemistry-driven industries.

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