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CS-W001157 4
Total: USD 88.00

4-Ethynylbenzaldehyde

  • CAS No. 63697-96-1

  • Cat. No. CS-W008115
  • Purity≥95%
  • MDL No.MFCD05664348

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

4-Ethynylbenzaldehyde|CS-W008115

Structure of 63697-96-1

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General Information

  • CAS No. 63697-96-1
  • Cat. No. CS-W008115
  • Purity ≥95%
  • MDL No. MFCD05664348
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₆O
  • Molecular Weight 130.14
  • Synonym(s) None
  • SMILES C#CC1=CC=C(C=O)C=C1

Description

4-Ethynylbenzaldehyde features a terminal alkyne group conjugated to an aromatic aldehyde, enabling efficient copper-catalyzed click reactions and Sonogashira couplings. This bifunctional scaffold integrates readily into complex molecular architectures under mild conditions, offering high chemoselectivity and stability during synthesis workflows.

Application

4-Ethynylbenzaldehyde serves as a versatile building block in transition-metal-catalyzed coupling reactions, enabling efficient access to conjugated enynes and extended π-systems. Its aldehyde functionality supports direct functionalization or conversion to hydrazones, while the terminal alkyne is compatible with Sonogashira, Glaser, and click chemistry protocols. The molecule exhibits excellent bench stability and facilitates straightforward purification, making it well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Wang, Xin; Ervithayasuporn, Vuthichai; Zhang, Yanhong; Kawakami, Yusuke Chemical Communications, 2011 , vol. 47, # 4 p. 1282 - 1284
  • Route2

    References

    • Tetrahedron Letters, , vol. 48, # 33 p. 5817 - 5820
  • Route3

    References

    • Journal of Organic Chemistry, , vol. 68, # 21 p. 8025 - 8036

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   17.07
  • LogP   1.4804
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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