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CS-W001157 4
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2-(Benzyloxy)-5-bromopyridine

  • CAS No. 83664-33-9

  • Cat. No. CS-W005570
  • Purity≥98%
  • MDL No.MFCD09037462

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

2-(Benzyloxy)-5-bromopyridine|CS-W005570

Structure of 83664-33-9

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General Information

  • CAS No. 83664-33-9
  • Cat. No. CS-W005570
  • Purity ≥98%
  • MDL No. MFCD09037462
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₀BrNO
  • Molecular Weight 264.12
  • Synonym(s) 2-Benzyloxy-5-bromopyridine
  • SMILES BrC1=CN=C(OCC2=CC=CC=C2)C=C1

Description

2-(Benzyloxy)-5-bromopyridine features a benzyl ether-linked pyridine core with a bromine substituent at the para position relative to the ether. This configuration enables direct functionalization in cross-coupling reactions, offering high reactivity under palladium catalysis. The benzyloxy group enhances solubility and stability during synthesis.

Application

2-(Benzyloxy)-5-bromopyridine serves as a versatile building block for C–H functionalization and cross-coupling reactions, enabling efficient access to substituted pyridine scaffolds. The benzyloxy group provides orthogonal protection for phenolic functionalities, while the bromide supports palladium-catalyzed coupling with broad functional group tolerance. Bench-stable and readily purified by column chromatography, it facilitates scalable synthesis of advanced intermediates in medicinal chemistry and agrochemical development.

Synthesis

  • Route1

    References

    • Ueda, Mikio; Mochida, Tomoyuki; Mori, Hatsumi Polyhedron, 2013 , vol. 52, p. 755 - 760
  • Route2

    References

    • EP1439175 A1, ; Page 46-47 ;
  • Route3

    References

    • Nara, Susheel J.; Jha, Mukund; Brinkhorst, Johan; Zemanek, Tony J.; Pratt, Derek A. Journal of Organic Chemistry, 2008 , vol. 73, # 23 p. 9326 - 9333

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

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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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