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CS-W001157 4
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3-(Pyridin-3-yl)prop-2-ynoic acid

  • CAS No. 59608-01-4

  • Cat. No. CS-0122143
  • Purity≥98%
  • MDL No.MFCD02177466

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

3-(Pyridin-3-yl)prop-2-ynoic acid|CS-0122143

Structure of 59608-01-4

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General Information

  • CAS No. 59608-01-4
  • Cat. No. CS-0122143
  • Purity ≥98%
  • MDL No. MFCD02177466
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₅NO₂
  • Molecular Weight 147.13
  • Synonym(s) 3-(Pyridin-3-yl)propiolic acid
  • SMILES O=C(O)C#CC1=CC=CN=C1

Description

This pyridyl-substituted propiolic acid features a conjugated alkyne-carboxylic acid motif that enables efficient coupling in click chemistry and transition metal-catalyzed transformations. The electron-deficient pyridine ring enhances reactivity in nucleophilic additions, while the terminal alkyne supports robust Sonogashira couplings. Bench-stable and moisture-tolerant, it serves as a versatile building block for bioconjugation and materials synthesis.

Application

3-(Pyridin-3-yl)prop-2-ynoic acid serves as a versatile building block for conjugated systems, enabling efficient access to heterocyclic scaffolds via [2+2] cycloadditions and Sonogashira coupling reactions. Its terminal alkyne and carboxylic acid functionalities offer orthogonal reactivity, facilitating modular synthesis of bioactive molecules. The compound exhibits good bench stability and is readily purified by recrystallization, making it well-suited for iterative synthetic workflows in medicinal chemistry and materials science.

Synthesis

  • Route1

    References

    • Babin; Dunogues; Duboudain Journal of Heterocyclic Chemistry, 1981 , vol. 18, # 3 p. 519 - 523
  • Route2
    • In-stock
      3-Bromopyridine|CS-0008362
      626-55-1
    • null|null
      471-25-0
    • ~%
    • In-stock
      3-(Pyridin-3-yl)prop-2-ynoic acid|CS-0122143
      59608-01-4

    References

    • Tartaggia, Stefano; De Lucchi, Ottorino; Goossen, Lukas J. European Journal of Organic Chemistry, 2012 , # 7 p. 1431 - 1438
  • Route3
    • Methyl 3-(pyridin-3-yl)propiolate|CS-0466437
      78584-30-2
    • ~69%
    • In-stock
      3-(Pyridin-3-yl)prop-2-ynoic acid|CS-0122143
      59608-01-4

    References

    • Babin; Dunogues; Duboudain Journal of Heterocyclic Chemistry, 1981 , vol. 18, # 3 p. 519 - 523

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
Precautionary Statements : P264-P270-P330-P501

Quality Control

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Computational Chemistry Data

  • TPSA   50.19
  • LogP   0.5177
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   0

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