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CS-W001157 4
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5-Ethynylpyridin-2-amine

  • CAS No. 82454-61-3

  • Cat. No. CS-W018832
  • Purity≥97%
  • MDL No.MFCD13175209

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

5-Ethynylpyridin-2-amine|CS-W018832

Structure of 82454-61-3

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General Information

  • CAS No. 82454-61-3
  • Cat. No. CS-W018832
  • Purity ≥97%
  • MDL No. MFCD13175209
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₆N₂
  • Molecular Weight 118.14
  • Synonym(s) 5-Ethynyl-pyridin-2-ylamine
  • SMILES NC1=NC=C(C=C1)C#C

Description

5-Ethynylpyridin-2-amine features a pyridine ring bearing both an ethynyl group and a primary amine at the 5- and 2-positions, respectively. This bifunctional architecture enables direct incorporation into click chemistry workflows, particularly CuAAC reactions. The electron-deficient pyridine enhances reactivity in conjugation processes while maintaining bench-stability under standard conditions.

Application

5-Ethynylpyridin-2-amine serves as a versatile building block in transition-metal-catalyzed coupling reactions, enabling efficient access to conjugated heterocyclic systems. The terminal alkyne group facilitates Sonogashira and CuAAC transformations, while the pyridin-2-amine moiety provides a readily functionalizable nitrogen site for derivatization. Its bench-stable nature and compatibility with diverse reaction conditions make it a practical choice for constructing bioactive scaffolds and advanced intermediates in medicinal chemistry workflows.

Synthesis

  • Route1
    • 5-((Trimethylsilyl)ethynyl)pyridin-2-amine|CS-0473513
      457628-40-9
    • ~96%
    • In-stock
      5-Ethynylpyridin-2-amine|CS-W018832
      82454-61-3

    References

    • Eisai RandD Management Co., Ltd. Patent: US2007/105904 A1, 2007 ; Location in patent: Page/Page column 74 ;
  • Route2
    • null|null
      911114-11-9
    • ~89%
    • In-stock
      5-Ethynylpyridin-2-amine|CS-W018832
      82454-61-3

    References

    • Hoffmann-La Roche Inc; Bachmann, Stephan; Bailey, Daniel; Brice, Jodie; Cedilote, Miall; Dong, Zhiming; Hildbrand, Stefan; Miller, Doreen; Spurr, Paul; Srivastava, Amit; Wichmann, Juergen; Woltering, Thomas; Yang, Jason; Zhang, Pingsheng Patent: US2013/85278 A1, 2013 ; Location in patent: Paragraph 0131; 0133 ;
  • Route3

    References

    • Matulenko, Mark A.; Paight, Ernest S.; Frey, Robin R.; Gomtsyan, Arthur; DiDomenico Jr., Stanley; Jiang, Meiqun; Lee, Chih-Hung; Stewart, Andrew O.; Yu, Haixia; Kohlhaas, Kathy L.; Alexander, Karen M.; McGaraughty, Steve; Mikusa, Joseph; Marsh, Kennan C.; Muchmore, Steven W.; Jakob, Clarissa L.; Kowaluk, Elizabeth A.; Jarvis, Michael F.; Bhagwat, Shripad S. Bioorganic and Medicinal Chemistry, 2007 , vol. 15, # 4 p. 1586 - 1605

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H302-H315-H320-H335
Precautionary Statements : P261-P280-P302+P352

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Computational Chemistry Data

  • TPSA   38.91
  • LogP   0.6451
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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