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CS-W001157 4
Total: USD 88.00

3-(P-tolyl)propiolic acid

  • CAS No. 2227-58-9

  • Cat. No. CS-W018356
  • Purity≥98%
  • MDL No.None

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

3-(P-tolyl)propiolic acid|CS-W018356

Structure of 2227-58-9

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General Information

  • CAS No. 2227-58-9
  • Cat. No. CS-W018356
  • Purity ≥98%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₈O₂
  • Molecular Weight 160.17
  • Synonym(s) 3-(4-Methylphenyl)prop-2-ynoic acid
  • SMILES O=C(O)C#CC1=CC=C(C)C=C1

Description

3-(p-Tolyl)propiolic acid is a sterically hindered alkyne featuring a para-tolyl group conjugated to a terminal acetylene. This electron-rich moiety enables efficient copper-catalyzed coupling reactions, facilitating rapid access to complex aryl-substituted alkynes under mild conditions. The molecule exhibits excellent bench stability and compatibility with diverse reaction environments.

Application

3-(p-Tolyl)propiolic acid serves as a versatile building block for synthesizing conjugated enynes, heterocycles, and functionalized alkynes. Its terminal alkyne moiety enables reliable copper-catalyzed coupling reactions, while the para-tolyl group provides steric and electronic stability. The compound exhibits excellent bench stability, facilitates straightforward purification, and functions effectively in standard Sonogashira and Huisgen cycloadditions.

Synthesis

  • Route1
    • null|null
      124-38-9
    • In-stock
      1-Ethynyl-4-methylbenzene|CS-W013610
      766-97-2
    • ~97%
    • In-stock
      3-(P-tolyl)propiolic acid|CS-W018356
      2227-58-9

    References

    • BASF SE; Goossen, Lukas J; Rodriguez Garrido, Nuria; Manjolinho Costa, Filipe; Lange, Paul P. Patent: US2014/12000 A1, 2014 ; Location in patent: Paragraph 0147 - 0151; 0152 ;
  • Route2
    • In-stock
      1-Iodo-4-methylbenzene|CS-W009210
      624-31-7
    • null|null
      471-25-0
    • ~71%
    • In-stock
      3-(P-tolyl)propiolic acid|CS-W018356
      2227-58-9

    References

    • Park, Kyungho; Palani, Thiruvengadam; Pyo, Ayoung; Lee, Sunwoo Tetrahedron Letters, 2012 , vol. 53, # 7 p. 733 - 737
  • Route3
    • null|null
      106-38-7
    • null|null
      471-25-0
    • ~74%
    • In-stock
      3-(P-tolyl)propiolic acid|CS-W018356
      2227-58-9

    References

    • Park, Kyungho; You, Jung-Min; Jeon, Seungwon; Lee, Sunwoo European Journal of Organic Chemistry, 2013 , # 10 p. 1973 - 1978

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-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   37.3
  • LogP   1.43112
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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