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CS-W001157 4
Total: USD 88.00

3,5-Dibromo-4-methoxypyridine

  • CAS No. 25813-24-5

  • Cat. No. CS-W021809
  • Purity≥97%
  • MDL No.MFCD13185524

*For research and further manufacturing use only, not for direct human use.

3,5-Dibromo-4-methoxypyridine|CS-W021809

Structure of 25813-24-5

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General Information

  • CAS No. 25813-24-5
  • Cat. No. CS-W021809
  • Purity ≥97%
  • MDL No. MFCD13185524
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅Br₂NO
  • Molecular Weight 266.92
  • Synonym(s) 3,5-DibroMo-4-Methoxy-pyridine
  • SMILES COC1=C(Br)C=NC=C1Br

Description

3,5-Dibromo-4-methoxypyridine features a pyridine core functionalized with bromine atoms at positions 3 and 5, paired with a methoxy group at C4. This electron-deficient heterocycle serves as a key building block for cross-coupling reactions, enabling efficient access to complex pharmaceutical intermediates under palladium-catalyzed conditions.

Application

3,5-Dibromo-4-methoxypyridine serves as a versatile building block in medicinal chemistry and materials science, enabling palladium-catalyzed cross-coupling reactions due to its orthogonal halogen reactivity. The methoxy group enhances solubility and modulates electronic properties, while the dibromo substitution pattern facilitates sequential functionalization. Bench-stable and readily purified by flash chromatography, it functions reliably in Suzuki-Miyaura, Stille, and Negishi couplings for constructing complex heterocyclic architectures.

Synthesis

  • Route1
    • null|null
      67-56-1
    • 3,4,5-Tribromopyridine|CS-0195773
      2457-48-9
    • ~97%
    • In-stock
      3,5-Dibromo-4-methoxypyridine|CS-W021809
      25813-24-5

    References

    • BRISTOL-MYERS SQUIBB COMPANY; AUSTIN, Joel, Francis; SHARMA, Lisa, S.; BALOG, James, Aaron; HUANG, Audris; VELAPARTHI, Upender; DARNE, Chetan, Padmakar; SAULNIER, Mark, George Patent: WO2012/15723 A1, 2012 ; Location in patent: Page/Page column 93 ; WO 2012/015723 A1
  • Route2

    References

    • BRISTOL-MYERS SQUIBB COMPANY; AUSTIN, Joel, Francis; SHARMA, Lisa, S.; BALOG, James, Aaron; HUANG, Audris; VELAPARTHI, Upender; DARNE, Chetan, Padmakar; SAULNIER, Mark, George Patent: WO2012/15723 A1, 2012 ; WO 2012/015723 A1
  • Route3

    References

    • BRISTOL-MYERS SQUIBB COMPANY; AUSTIN, Joel, Francis; SHARMA, Lisa, S.; BALOG, James, Aaron; HUANG, Audris; VELAPARTHI, Upender; DARNE, Chetan, Padmakar; SAULNIER, Mark, George Patent: WO2012/15723 A1, 2012 ; WO 2012/015723 A1

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   22.12
  • LogP   2.6152
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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