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CS-W001157 4
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Methyl 5-ethynylpicolinate

  • CAS No. 17880-61-4

  • Cat. No. CS-0043882
  • Purity≥98%
  • MDL No.MFCD13189756

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

Methyl 5-ethynylpicolinate|CS-0043882

Structure of 17880-61-4

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General Information

  • CAS No. 17880-61-4
  • Cat. No. CS-0043882
  • Purity ≥98%
  • MDL No. MFCD13189756
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₇NO₂
  • Molecular Weight 161.16
  • Synonym(s) Methyl 5-ethynylpyridine-2-carboxylate
  • SMILES O=C(OC)C1=NC=C(C#C)C=C1

Description

Methyl 5-ethynylpicolinate is a synthetically valuable pyridine derivative featuring a terminal alkyne group at the 5-position. This functionality enables efficient copper-catalyzed azide-alkyne cycloaddition (CuAAC) for bioconjugation and click chemistry applications. The ester moiety offers compatibility with nucleophilic transformations, while the electron-deficient pyridine ring enhances reactivity in cross-coupling processes.

Application

Methyl 5-ethynylpicolinate serves as a versatile building block in synthetic organic chemistry, enabling efficient access to functionalized heterocycles via copper-catalyzed azide-alkyne cycloaddition (CuAAC) and other alkyne-directed transformations. Its terminal alkyne group exhibits excellent stability under standard reaction conditions and facilitates straightforward purification. The ester functionality supports further derivatization, including hydrolysis and coupling reactions, making it valuable for constructing bioactive scaffolds and advanced intermediates in medicinal chemistry and materials science.

Synthesis

  • Route1

    References

    • Journal of Organometallic Chemistry, , vol. 696, # 25 p. 4039 - 4045
  • Route2

    References

    • WO2012/31298 A2, ; WO 2012/031298 A2

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

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Computational Chemistry Data

  • TPSA   39.19
  • LogP   0.8495
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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