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CS-W001157 4
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5-Bromo-2-ethynylpyridine

  • CAS No. 111770-86-6

  • Cat. No. CS-0043016
  • Purity≥98%
  • MDL No.MFCD03095276

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

5-Bromo-2-ethynylpyridine|CS-0043016

Structure of 111770-86-6

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General Information

  • CAS No. 111770-86-6
  • Cat. No. CS-0043016
  • Purity ≥98%
  • MDL No. MFCD03095276
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄BrN
  • Molecular Weight 182.02
  • Synonym(s) 2-Ethynyl-5-bromopyridine
  • SMILES C#CC1=NC=C(Br)C=C1

Description

5-Bromo-2-ethynylpyridine features a strategically positioned ethynyl group flanked by a bromine substituent, enabling efficient copper-catalyzed coupling reactions. This electron-deficient pyridine scaffold delivers high reactivity in click chemistry and transition-metal-mediated transformations, facilitating the construction of complex heterocyclic architectures under mild conditions.

Application

5-Bromo-2-ethynylpyridine serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient construction of biaryl and heteroaryl architectures. The ethynyl group facilitates Sonogashira coupling with aryl halides, while the bromopyridine moiety supports Suzuki-Miyaura and Negishi couplings. Its bench-stable nature and compatibility with diverse functional groups make it ideal for modular synthesis of complex pharmaceutical scaffolds and advanced ligands.

Synthesis

  • Route1
    • 5-Bromo-2-((trimethylsilyl)ethynyl)pyridine|CS-0686653
      111770-80-0
    • ~94%
    • In-stock
      5-Bromo-2-ethynylpyridine|CS-0043016
      111770-86-6

    References

    • Tilley, Jefferson W.; Zawoiski, Sonja Journal of Organic Chemistry, 1988 , vol. 53, # 2 p. 386 - 390
  • Route2
    • In-stock
      5-Bromo-2-iodopyridine|CS-W002668
      223463-13-6
    • null|null
      1066-54-2
    • ~%
    • In-stock
      5-Bromo-2-ethynylpyridine|CS-0043016
      111770-86-6

    References

    • Catalysis Communications, , vol. 47, p. 40 - 44
  • Route3
    • null|null
      866929-82-0
    • ~78%
    • In-stock
      5-Bromo-2-ethynylpyridine|CS-0043016
      111770-86-6

    References

    • Sooksawat, Dhassida; Pike, Sarah J.; Slawin, Alexandra M.Z.; Lusby, Paul J. Chemical Communications, 2013 , vol. 49, # 94 p. 11077 - 11079

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   12.89
  • LogP   1.8254
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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