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CS-W001157 4
Total: USD 88.00

2-Ethynyl-5-fluoropyridine

  • CAS No. 884494-34-2

  • Cat. No. CS-0019347
  • Purity≥98%
  • MDL No.MFCD03095259

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

2-Ethynyl-5-fluoropyridine|CS-0019347

Structure of 884494-34-2

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General Information

  • CAS No. 884494-34-2
  • Cat. No. CS-0019347
  • Purity ≥98%
  • MDL No. MFCD03095259
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄FN
  • Molecular Weight 121.11
  • Synonym(s) None
  • SMILES FC1=CN=C(C#C)C=C1

Description

2-Ethynyl-5-fluoropyridine features a conjugated alkyne linked to a fluorinated pyridine ring, enabling efficient coupling in transition-metal-catalyzed reactions. The electron-deficient heterocycle enhances reactivity in cross-coupling processes, while the terminal alkyne facilitates derivatization under mild conditions. This compound serves as a key building block for functionalized aromatic systems in medicinal chemistry and materials science.

Application

2-Ethynyl-5-fluoropyridine serves as a versatile building block in synthetic organic chemistry, enabling palladium-catalyzed cross-coupling reactions such as Sonogashira and Suzuki-Miyaura transformations. The fluorinated pyridine core provides enhanced electronic effects and metabolic stability, while the terminal alkyne functionality offers high reactivity and compatibility with diverse functional groups. This compound exhibits excellent bench stability and facilitates efficient access to complex heterocyclic scaffolds relevant to medicinal chemistry and materials science.

Synthesis

  • Route1
    • In-stock
      5-Fluoropicolinaldehyde|CS-W004870
      31181-88-1
    • null|null
      90965-06-3
    • ~77%
    • In-stock
      2-Ethynyl-5-fluoropyridine|CS-0019347
      884494-34-2

    References

    • F. HOFFMANN-LA ROCHE AG; HERNANDEZ, Maria-Clemencia; LUCAS, Matthew C.; THOMAS, Andrew Patent: WO2012/62687 A1, 2012 ; Location in patent: Page/Page column 51 ; WO 2012/062687 A1
  • Route2
    • null|null
      904694-30-0
    • ~61%
    • In-stock
      2-Ethynyl-5-fluoropyridine|CS-0019347
      884494-34-2

    References

    • Ube Industries, Ltd. Patent: EP1847545 A1, 2007 ; Location in patent: Page/Page column 39 ;
  • Route3
    • 5-Fluoro-2-((trimethylsilyl)ethynyl)pyridine|CS-1192831
      884494-40-0
    • ~%
    • In-stock
      2-Ethynyl-5-fluoropyridine|CS-0019347
      884494-34-2

    References

    • Roese, Philipp; Puenner, Florian; Hilt, Gerhard; Harms, Klaus Synlett, 2013 , vol. 24, # 9 art. no. ST-2013-B0156-L, p. 1101 - 1104

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   1.202
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   0

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