Cas no 1211542-16-3 (3-Bromo-2-iodo-5-methylpyridine)

3-Bromo-2-iodo-5-methylpyridine is a halogenated pyridine derivative with significant utility in synthetic organic chemistry. Its distinct substitution pattern, featuring bromine and iodine at the 3- and 2-positions alongside a methyl group at the 5-position, makes it a versatile intermediate for cross-coupling reactions, such as Suzuki-Miyaura or Sonogashira couplings. The electron-withdrawing halogens enhance reactivity in nucleophilic aromatic substitutions, while the methyl group offers steric and electronic modulation. This compound is particularly valuable in pharmaceutical and agrochemical research for constructing complex heterocyclic frameworks. High purity and stability under standard conditions ensure reliable performance in demanding synthetic applications.
3-Bromo-2-iodo-5-methylpyridine structure
1211542-16-3 structure
Product Name:3-Bromo-2-iodo-5-methylpyridine
CAS No:1211542-16-3
MF:C6H5BrIN
MW:297.91907286644
MDL:MFCD16610048
CID:2952836
PubChem ID:23542450
Update Time:2025-11-06

3-Bromo-2-iodo-5-methylpyridine Chemical and Physical Properties

Names and Identifiers

    • 3-溴-2-碘-5-甲基吡啶
    • 3-bromo-2-iodo-5-methylpyridine
    • 1211542-16-3
    • F76904
    • MFCD16610048
    • 3-Bromo-2-iodo-5-methylpyridine
    • MDL: MFCD16610048
    • Inchi: 1S/C6H5BrIN/c1-4-2-5(7)6(8)9-3-4/h2-3H,1H3
    • InChI Key: JACWOENAIROMAI-UHFFFAOYSA-N
    • SMILES: IC1=C(C=C(C=N1)C)Br

Computed Properties

  • Exact Mass: 296.86501g/mol
  • Monoisotopic Mass: 296.86501g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 9
  • Rotatable Bond Count: 0
  • Complexity: 99.1
  • 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: 2.6
  • Topological Polar Surface Area: 12.9

3-Bromo-2-iodo-5-methylpyridine Pricemore >>

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Additional information on 3-Bromo-2-iodo-5-methylpyridine

Recent Advances in the Application of 3-Bromo-2-iodo-5-methylpyridine (CAS: 1211542-16-3) in Chemical Biology and Pharmaceutical Research

3-Bromo-2-iodo-5-methylpyridine (CAS: 1211542-16-3) is a halogenated pyridine derivative that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound serves as a crucial building block in the synthesis of complex molecules, particularly in the development of novel drug candidates and bioactive probes. Its unique structural features, including the presence of both bromine and iodine substituents, make it an attractive intermediate for cross-coupling reactions and other transformative chemical processes.

Recent studies have highlighted the role of 3-Bromo-2-iodo-5-methylpyridine in the synthesis of kinase inhibitors, which are pivotal in targeting various cancer pathways. For instance, a 2023 study published in the Journal of Medicinal Chemistry demonstrated its utility in the construction of pyridine-based scaffolds that exhibit potent inhibitory activity against tyrosine kinases. The researchers employed palladium-catalyzed cross-coupling reactions to functionalize the compound, yielding derivatives with enhanced selectivity and efficacy.

In addition to its applications in drug discovery, 3-Bromo-2-iodo-5-methylpyridine has been utilized in the development of fluorescent probes for imaging applications. A recent publication in Chemical Communications detailed its incorporation into a probe designed for the detection of reactive oxygen species (ROS) in cellular environments. The probe's high sensitivity and specificity were attributed to the strategic placement of the bromine and iodine atoms, which facilitated efficient electron transfer processes.

The compound's stability and reactivity have also been explored in the context of material science. A 2022 study in ACS Applied Materials & Interfaces reported its use as a precursor for the synthesis of organic semiconductors. The researchers noted that the halogen atoms in 3-Bromo-2-iodo-5-methylpyridine played a critical role in tuning the electronic properties of the resulting materials, making them suitable for optoelectronic applications.

Despite its promising applications, challenges remain in the large-scale synthesis and purification of 3-Bromo-2-iodo-5-methylpyridine. Recent advancements in flow chemistry and catalytic methodologies, however, are addressing these limitations. A 2023 review in Organic Process Research & Development highlighted innovative approaches to streamline its production, emphasizing the importance of green chemistry principles in reducing waste and improving yield.

In conclusion, 3-Bromo-2-iodo-5-methylpyridine (CAS: 1211542-16-3) continues to be a valuable tool in chemical biology and pharmaceutical research. Its multifaceted applications, from drug development to material science, underscore its significance in advancing scientific and technological frontiers. Ongoing research efforts are expected to further elucidate its potential and expand its utility in diverse fields.

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