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CS-W001157 4
Total: USD 88.00

2-Bromo-6-ethynylpyridine

  • CAS No. 445468-63-3

  • Cat. No. CS-0158553
  • Molecule weight182.02
  • Purity≥97%
  • MDL No.None

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

2-Bromo-6-ethynylpyridine|CS-0158553

Structure of 445468-63-3

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General Information

  • CAS No. 445468-63-3
  • Cat. No. CS-0158553
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄BrN
  • Molecular Weight 182.02
  • Synonym(s) PYRIDINE,2-BROMO-6-ETHYNYL
  • SMILES C#CC1=NC(=CC=C1)Br

Description

2-Bromo-6-ethynylpyridine features a bromine substituent and terminal alkyne group positioned ortho to each other on the pyridine ring, enabling efficient copper-catalyzed coupling reactions. The electron-deficient pyridine core enhances reactivity in cross-coupling processes, while the ethynyl moiety provides a robust handle for further functionalization. This compound serves as a key building block in synthesizing conjugated systems for materials science and pharmaceutical applications.

Application

2-Bromo-6-ethynylpyridine serves as a versatile building block in transition-metal-catalyzed cross-coupling reactions, enabling efficient construction of conjugated biaryl and heteroaryl architectures. The bromine and terminal alkyne functionalities offer orthogonal reactivity, facilitating sequential coupling strategies. Its bench-stable nature and compatibility with palladium- and copper-based catalysis make it well-suited for iterative synthesis of complex scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • 2-Bromo-6-((trimethylsilyl)ethynyl)pyridine|CS-1038805
      445468-65-5
    • ~29%
    • In-stock
      2-Bromo-6-ethynylpyridine|CS-0158553
      445468-63-3

    References

    • Dana, Bogdan H; Robinson, Brian H; Simpson, Jim Journal of Organometalic Chemistry, 2002 , vol. 648, # 1-2 p. 251 - 269
  • Route2

    References

    • Orita, Akihiro; Ye, Fangguo; Babu, Govindarajulu; Ikemoto, Tomohiro; Otera, Junzo Canadian Journal of Chemistry, 2005 , vol. 83, # 6-7 p. 716 - 727
  • Route3
    • In-stock
      2,6-Dibromopyridine|CS-W008833
      626-05-1
    • null|null
      1066-54-2
    • ~75%
    • In-stock
      2-Bromo-6-ethynylpyridine|CS-0158553
      445468-63-3

    References

    • Orita, Akihiro; Nakano, Takehiko; Yokoyama, Taisaku; Babu, Govindarajulu; Otera, Junzo Chemistry Letters, 2004 , vol. 33, # 10 art. no. CL-040868, p. 1298 - 1299

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-P330-P362+P364-P405-P501

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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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