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CS-W001157 4
Total: USD 88.00

5-(Benzyloxy)-2-bromopyridine

  • CAS No. 630120-99-9

  • Cat. No. CS-0046861
  • Purity≥98%
  • MDL No.MFCD11874623

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

5-(Benzyloxy)-2-bromopyridine|CS-0046861

Structure of 630120-99-9

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General Information

  • CAS No. 630120-99-9
  • Cat. No. CS-0046861
  • Purity ≥98%
  • MDL No. MFCD11874623
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₀BrNO
  • Molecular Weight 264.12
  • Synonym(s) HDH-PHARMA 24754
  • SMILES BrC1=NC=C(OCC2=CC=CC=C2)C=C1

Description

5-(Benzyloxy)-2-bromopyridine features a bromine atom at the 2-position and a benzyloxy group at the 5-position, enabling selective cross-coupling reactions. This electron-deficient pyridine scaffold integrates readily into complex heterocycles under palladium catalysis, offering high functional group tolerance and stability under standard reaction conditions.

Application

5-(Benzyloxy)-2-bromopyridine serves as a versatile building block in medicinal chemistry, enabling palladium-catalyzed cross-coupling reactions due to its stable bromo functionality. The benzyloxy group provides orthogonal protection and enhances solubility, facilitating downstream transformations. Its bench-stable nature and compatibility with standard synthetic protocols make it ideal for constructing complex heterocyclic scaffolds in API development.

Synthesis

  • Route1
    • In-stock
      6-Bromopyridin-3-ol|CS-D0986
      55717-45-8
    • null|null
      100-39-0
    • ~100%
    • In-stock
      5-(Benzyloxy)-2-bromopyridine|CS-0046861
      630120-99-9

    References

    • BAYER PHARMA AKTIENGESELLSCHAFT; SCHMITT-WILLICH, Heribert; HEINRICH, Tobias; BROCKSCHNIEDER, Damian Patent: WO2011/110511 A1, 2011 ; Location in patent: Page/Page column 21-22 ;
  • Route2

    References

    • MERCK and CO., INC. Patent: WO2009/140163 A1, 2009 ; Location in patent: Page/Page column 37 ; WO 2009/140163 A1
  • Route3

    References

    • Patel, Meena V.; Kolasa, Teodozyj; Mortell, Kathleen; Matulenko, Mark A.; Hakeem, Ahmed A.; Rohde, Jeffrey J.; Nelson, Sherry L.; Cowart, Marlon D.; Nakane, Masaki; Miller, Loan N.; Uchic, Marie E.; Terranova, Marc A.; El-Kouhen, Odile F.; Donnelly-Roberts, Diana L.; Namovic, Marian T.; Hollingsworth, Peter R.; Chang, Renjie; Martino, Brenda R.; Wetter, Jill M.; Marsh, Kennan C.; Martin, Ruth; Darbyshire, John F.; Gintant, Gary; Hsieh, Gin C.; Moreland, Robert B.; Sullivan, James P.; Brioni, Jorge D.; Stewart, Andrew O. Journal of Medicinal Chemistry, 2006 , vol. 49, # 25 p. 7450 - 7465

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   3.4231
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   3

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