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CS-W001157 4
Total: USD 88.00

3-(4-Methoxyphenyl)prop-2-ynoic acid

  • CAS No. 2227-57-8

  • Cat. No. CS-0122129
  • Molecule weight176.17
  • Purity≥95%
  • MDL No.MFCD00181523

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

3-(4-Methoxyphenyl)prop-2-ynoic acid|CS-0122129

Structure of 2227-57-8

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General Information

  • CAS No. 2227-57-8
  • Cat. No. CS-0122129
  • Purity ≥95%
  • MDL No. MFCD00181523
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₈O₃
  • Molecular Weight 176.17
  • Synonym(s) 3-(4-Methoxyphenyl)propiolic acid
  • SMILES O=C(O)C#CC1=CC=C(OC)C=C1

Description

This propargylic acid features a para-methoxyphenyl group that enhances solubility and modulates electronic properties. The terminal alkyne enables efficient coupling in copper-catalyzed reactions, while the carboxylic acid facilitates conjugation or derivatization under standard conditions.

Application

3-(4-Methoxyphenyl)prop-2-ynoic acid serves as a versatile building block for the synthesis of conjugated enynes and heterocyclic systems. Its terminal alkyne functionality enables efficient copper-catalyzed azide-alkyne cycloaddition (CuAAC), while the para-methoxyaryl group provides electronic stabilization and enhanced solubility. The carboxylic acid moiety facilitates direct derivatization or activation for amide bond formation, offering robust utility in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • null|null
      124-38-9
    • In-stock
      4-Ethynylanisole|CS-W004104
      768-60-5
    • ~96%
    • In-stock
      3-(4-Methoxyphenyl)prop-2-ynoic acid|CS-0122129
      2227-57-8

    References

    • EURO-CELTIQUE S.A. Patent: WO2005/56524 A2, 2005 ; Location in patent: Page/Page column 114 ;
  • Route2
    • null|null
      60512-57-4
    • null|null
      124-38-9
    • ~93%
    • In-stock
      3-(4-Methoxyphenyl)prop-2-ynoic acid|CS-0122129
      2227-57-8

    References

    • Nissan Chemical Industries, Ltd. Patent: US2009/23939 A1, 2009 ; Location in patent: Page/Page column 20 ;
  • Route3
    • In-stock
      4-Iodoanisole|CS-W003965
      696-62-8
    • null|null
      471-25-0
    • ~65%
    • In-stock
      3-(4-Methoxyphenyl)prop-2-ynoic acid|CS-0122129
      2227-57-8

    References

    • Park, Kyungho; Palani, Thiruvengadam; Pyo, Ayoung; Lee, Sunwoo Tetrahedron Letters, 2012 , vol. 53, # 7 p. 733 - 737

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   46.53
  • LogP   1.1313
  • H_Acceptors   2
  • H_Donors   1
  • Rotatable_Bonds   1

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