Cas no 2385454-43-1 (5-bromo-3-iodo-2-methoxy-4-methylpyridine)

5-Bromo-3-iodo-2-methoxy-4-methylpyridine is a halogenated pyridine derivative with a distinct substitution pattern, offering versatility in synthetic organic chemistry. The presence of bromine and iodine at the 5- and 3-positions, respectively, provides reactive handles for cross-coupling reactions, such as Suzuki or Sonogashira couplings, enabling further functionalization. The methoxy group at the 2-position enhances electron density, influencing reactivity and selectivity in nucleophilic substitutions. The methyl group at the 4-position contributes to steric and electronic modulation, making this compound valuable for pharmaceutical and agrochemical intermediates. Its well-defined structure ensures consistent performance in complex synthetic routes, supporting precise molecular design.
5-bromo-3-iodo-2-methoxy-4-methylpyridine structure
2385454-43-1 structure
Product Name:5-bromo-3-iodo-2-methoxy-4-methylpyridine
CAS No:2385454-43-1
MF:C7H7BrINO
MW:327.945053339005
CID:6302568
PubChem ID:134818915
Update Time:2025-06-08

5-bromo-3-iodo-2-methoxy-4-methylpyridine Chemical and Physical Properties

Names and Identifiers

    • 5-bromo-3-iodo-2-methoxy-4-methylpyridine
    • EN300-22847555
    • 2385454-43-1
    • Inchi: 1S/C7H7BrINO/c1-4-5(8)3-10-7(11-2)6(4)9/h3H,1-2H3
    • InChI Key: GMKXJQJHJIYMAU-UHFFFAOYSA-N
    • SMILES: IC1C(=NC=C(C=1C)Br)OC

Computed Properties

  • Exact Mass: 326.87557g/mol
  • Monoisotopic Mass: 326.87557g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 1
  • Complexity: 136
  • 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: 2.9
  • Topological Polar Surface Area: 22.1?2

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Additional information on 5-bromo-3-iodo-2-methoxy-4-methylpyridine

Recent Advances in the Study of 5-Bromo-3-Iodo-2-Methoxy-4-Methylpyridine (CAS: 2385454-43-1) in Chemical Biology and Pharmaceutical Research

The compound 5-bromo-3-iodo-2-methoxy-4-methylpyridine (CAS: 2385454-43-1) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural properties and potential applications in drug discovery. This heterocyclic compound, characterized by its halogen-substituted pyridine core, serves as a versatile intermediate in the synthesis of complex molecules, particularly in the development of kinase inhibitors and other therapeutic agents. Recent studies have explored its reactivity, biological activity, and utility in medicinal chemistry, positioning it as a promising candidate for further investigation.

One of the key areas of focus has been the use of 5-bromo-3-iodo-2-methoxy-4-methylpyridine in cross-coupling reactions, such as Suzuki-Miyaura and Sonogashira couplings, which are pivotal for constructing biaryl and alkynyl frameworks in drug molecules. A 2023 study published in the Journal of Medicinal Chemistry demonstrated its efficacy as a substrate in palladium-catalyzed reactions, yielding high selectivity and functional group tolerance. The presence of both bromine and iodine substituents on the pyridine ring allows for sequential functionalization, enabling the synthesis of diverse derivatives with tailored pharmacological properties.

In addition to its synthetic utility, preliminary biological evaluations have revealed that derivatives of 5-bromo-3-iodo-2-methoxy-4-methylpyridine exhibit moderate inhibitory activity against certain protein kinases implicated in cancer and inflammatory diseases. For instance, a recent preprint on bioRxiv highlighted its role as a precursor in the development of selective JAK2 inhibitors, which are being investigated for their potential in treating myeloproliferative disorders. These findings underscore the compound's relevance in targeted therapy development.

Further investigations into the physicochemical properties of 5-bromo-3-iodo-2-methoxy-4-methylpyridine, including its solubility, stability, and metabolic profile, are currently underway. A collaborative effort between academic and industrial researchers, as reported in ACS Pharmacology & Translational Science, aims to optimize its pharmacokinetic parameters for in vivo applications. Such studies are critical for advancing this compound from a research tool to a clinically viable entity.

In conclusion, 5-bromo-3-iodo-2-methoxy-4-methylpyridine (CAS: 2385454-43-1) represents a valuable scaffold in modern drug discovery, with its dual functionality and adaptability in synthetic routes. Ongoing research is expected to uncover additional applications, particularly in the design of next-generation small-molecule therapeutics. Future directions may include computational modeling to predict its binding affinities and toxicity profiles, as well as expanded structure-activity relationship (SAR) studies to refine its biological potency.

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