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CS-W001157 4
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1-(4-Ethynylphenyl)ethanone

  • CAS No. 42472-69-5

  • Cat. No. CS-0063791
  • Purity≥95%
  • MDL No.MFCD04974025

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

1-(4-Ethynylphenyl)ethanone|CS-0063791

Structure of 42472-69-5

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General Information

  • CAS No. 42472-69-5
  • Cat. No. CS-0063791
  • Purity ≥95%
  • MDL No. MFCD04974025
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₈O
  • Molecular Weight None
  • Synonym(s) 4-Ethynylacetophenone
  • SMILES CC(C1=CC=C(C#C)C=C1)=O

Description

1-(4-Ethynylphenyl)ethanone features a conjugated alkyne linked directly to an aromatic ring, enabling efficient copper-catalyzed azide-alkyne cycloaddition (CuAAC). This electrophilic aryl ketone integrates readily into bioconjugation workflows and functional materials. The ethynyl group exhibits high reactivity under mild conditions, while the ketone moiety provides a handle for further derivatization. Bench-stable and moisture-tolerant, it streamlines synthesis in chemical biology and polymer science applications.

Application

1-(4-Ethynylphenyl)ethanone serves as a versatile building block in transition-metal-catalyzed coupling reactions, particularly enabling efficient Sonogashira and Glaser-type homocoupling processes. The conjugated alkyne functionality exhibits excellent bench stability and compatibility with diverse functional groups, facilitating straightforward purification and integration into complex molecular architectures. This compound functions as a key intermediate in the synthesis of substituted biaryls and extended π-conjugated systems relevant to materials science and medicinal chemistry applications.

Synthesis

  • Route1

    References

    • Dreyer, Daniel R.; Jia, Hong-Peng; Bielawski, Christopher W. Angewandte Chemie - International Edition, 2010 , vol. 49, # 38 p. 6813 - 6816
  • Route2
    • null|null
      95785-28-7
    • ~82%
    • In-stock
      1-(4-Ethynylphenyl)ethanone|CS-0063791
      42472-69-5

    References

    • Pourjavadi, Ali; Bagheri Marandi, Gholam Journal of Chemical Research - Part S, 2002 , # 11 p. 552 - 555
  • Route3
    • 1-(4-((Trimethylsilyl)ethynyl)phenyl)ethan-1-one|CS-1225425
      75883-03-3
    • ~96%
    • In-stock
      1-(4-Ethynylphenyl)ethanone|CS-0063791
      42472-69-5

    References

    • Xu, Caixia; Du, Weiyuan; Zeng, Yi; Dai, Bin; Guo, Hao Organic Letters, 2014 , vol. 16, # 3 p. 948 - 951

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 : P260-P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   17.07
  • LogP   1.8705
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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