Cas no 25813-24-5 (3,5-Dibromo-4-methoxypyridine)

3,5-Dibromo-4-methoxypyridine is a halogenated pyridine derivative with significant utility in organic synthesis and pharmaceutical research. Its brominated structure enhances reactivity in cross-coupling reactions, such as Suzuki or Stille couplings, making it a valuable intermediate for constructing complex heterocyclic frameworks. The methoxy group at the 4-position contributes to electronic modulation, influencing regioselectivity in subsequent functionalization. This compound is particularly useful in medicinal chemistry for the development of bioactive molecules due to its balanced reactivity and stability under standard reaction conditions. High purity grades ensure consistent performance in demanding applications, including ligand design and agrochemical synthesis.
3,5-Dibromo-4-methoxypyridine structure
3,5-Dibromo-4-methoxypyridine structure
Product Name:3,5-Dibromo-4-methoxypyridine
CAS No:25813-24-5
MF:C6H5Br2NO
MW:266.917999982834
MDL:MFCD13185524
CID:1026703
PubChem ID:21766026
Update Time:2025-11-02

3,5-Dibromo-4-methoxypyridine Chemical and Physical Properties

Names and Identifiers

    • 3,5-Dibromo-4-methoxypyridine
    • 3,5-DIBROMO-4-METHOXY-PYRIDINE
    • 3.5-Dibrom-4-methoxy-pyridin
    • 3,5-dibromo-4-methoxylpyridine
    • VITQLRNAXLKYCU-UHFFFAOYSA-N
    • AM62372
    • FCH1380694
    • AX8215240
    • ST24022470
    • Z4505
    • AKOS015999153
    • SY022884
    • 25813-24-5
    • DTXSID00617778
    • MFCD13185524
    • DA-43017
    • DS-1953
    • A905167
    • SCHEMBL527045
    • CS-W021809
    • MDL: MFCD13185524
    • Inchi: 1S/C6H5Br2NO/c1-10-6-4(7)2-9-3-5(6)8/h2-3H,1H3
    • InChI Key: VITQLRNAXLKYCU-UHFFFAOYSA-N
    • SMILES: BrC1C=NC=C(C=1OC)Br

Computed Properties

  • Exact Mass: 264.87400
  • Monoisotopic Mass: 264.87379g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 10
  • Rotatable Bond Count: 1
  • Complexity: 102
  • 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
  • Topological Polar Surface Area: 22.1
  • XLogP3: 2.2

Experimental Properties

  • PSA: 22.12000
  • LogP: 2.61520

3,5-Dibromo-4-methoxypyridine Security Information

3,5-Dibromo-4-methoxypyridine Customs Data

  • HS CODE:2933399090
  • Customs Data:

    China Customs Code:

    2933399090

    Overview:

    2933399090. Other compounds with non fused pyridine rings in structure. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

    Summary:

    2933399090. other compounds containing an unfused pyridine ring (whether or not hydrogenated) in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

3,5-Dibromo-4-methoxypyridine Pricemore >>

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3,5-Dibromo-4-methoxypyridine Production Method

Additional information on 3,5-Dibromo-4-methoxypyridine

3,5-Dibromo-4-methoxypyridine (CAS No. 25813-24-5): A Versatile Brominated Pyridine Derivative in Modern Chemistry

3,5-Dibromo-4-methoxypyridine (CAS No. 25813-24-5) is a halogenated pyridine derivative that has gained significant attention in pharmaceutical and agrochemical research. This compound, characterized by its bromine substitution pattern and methoxy functional group, serves as a crucial building block in organic synthesis. The molecular structure features two bromine atoms at the 3- and 5-positions and a methoxy group at the 4-position of the pyridine ring, creating unique electronic properties that make it valuable for various applications.

Recent studies highlight the growing importance of brominated pyridine compounds in drug discovery, particularly in the development of kinase inhibitors and antiviral agents. The 3,5-dibromo substitution pattern enhances the compound's reactivity in cross-coupling reactions, making it a preferred intermediate for Suzuki-Miyaura and Buchwald-Hartwig couplings. Researchers are particularly interested in how the 4-methoxy group influences the compound's electronic properties and its potential as a directing group in metal-catalyzed reactions.

The synthesis of 3,5-Dibromo-4-methoxypyridine typically involves bromination of 4-methoxypyridine under controlled conditions. Advanced purification techniques ensure high purity levels (>98%) required for pharmaceutical applications. Analytical characterization by 1H NMR, 13C NMR, and mass spectrometry confirms the structure and purity of this important intermediate. The compound's stability under various conditions makes it suitable for long-term storage and transportation.

In material science, 25813-24-5 has shown promise in the development of organic electronic materials. The electron-withdrawing nature of the bromine atoms combined with the electron-donating methoxy group creates interesting electronic properties for potential use in organic semiconductors. Recent patents demonstrate its application in creating novel photovoltaic materials and OLED components, addressing the growing demand for more efficient energy conversion technologies.

The global market for pyridine derivatives like 3,5-Dibromo-4-methoxypyridine is experiencing steady growth, driven by increasing R&D investments in pharmaceutical and agricultural chemistry. Manufacturers are focusing on developing more sustainable production methods to meet the rising demand while reducing environmental impact. Quality control standards have become more stringent, with HPLC purity requirements often exceeding 99% for high-end applications.

From a safety perspective, proper handling procedures should be followed when working with 3,5-Dibromo-4-methoxypyridine, including the use of personal protective equipment in laboratory settings. While not classified as highly hazardous, standard precautions for handling brominated compounds should be observed. The compound's Material Safety Data Sheet (MSDS) provides detailed information about storage conditions and handling recommendations.

Recent advancements in green chemistry have led to improved synthetic routes for 25813-24-5, reducing the use of hazardous reagents and minimizing waste generation. These developments align with the pharmaceutical industry's increasing focus on sustainable manufacturing practices. The compound's role in the synthesis of biologically active molecules continues to expand, particularly in the development of new antimicrobial agents.

Analytical method development for 3,5-Dibromo-4-methoxypyridine has progressed significantly, with modern techniques like UPLC-MS enabling more precise quantification in complex matrices. This is particularly important for quality control in pharmaceutical manufacturing where even trace impurities can affect drug efficacy. Stability studies indicate that the compound maintains its integrity under standard storage conditions for extended periods.

The unique properties of 3,5-Dibromo-4-methoxypyridine make it a subject of ongoing research in medicinal chemistry. Its molecular structure serves as an excellent scaffold for developing compounds with potential activity against various disease targets. The bromine atoms provide convenient sites for further functionalization through modern coupling reactions, while the methoxy group can be modified to fine-tune biological activity.

Looking ahead, the applications of 25813-24-5 are expected to expand into new areas such as bioconjugation chemistry and proteolysis targeting chimeras (PROTACs). The compound's versatility and well-characterized reactivity make it a valuable tool in these emerging fields. As synthetic methodologies continue to advance, 3,5-Dibromo-4-methoxypyridine will likely play an increasingly important role in the development of next-generation therapeutic agents and functional materials.

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