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CS-W001157 4
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2-(Phenylethynyl)benzaldehyde

  • CAS No. 59046-72-9

  • Cat. No. CS-0156581
  • Purity≥98%
  • MDL No.MFCD09030317

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

2-(Phenylethynyl)benzaldehyde|CS-0156581

Structure of 59046-72-9

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General Information

  • CAS No. 59046-72-9
  • Cat. No. CS-0156581
  • Purity ≥98%
  • MDL No. MFCD09030317
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₅H₁₀O
  • Molecular Weight 206.24
  • Synonym(s) 2-PHENYLETHYNYL-BENZALDEHYDE
  • SMILES C1=CC=C(C=C1)C#CC2=CC=CC=C2C=O

Description

2-(Phenylethynyl)benzaldehyde features a conjugated alkyne-aryl-aldehyde scaffold enabling efficient coupling reactions. This electron-deficient alkyne integrates readily into click chemistry protocols and serves as a key building block for functionalized aromatic systems in materials science and medicinal chemistry applications.

Application

2-(Phenylethynyl)benzaldehyde serves as a versatile building block in transition-metal-catalyzed coupling reactions, enabling efficient access to conjugated enynes and extended π-systems. The aldehyde functionality facilitates subsequent transformations such as Wittig reactions, reductive amination, or condensation with amines, while the terminal alkyne supports Sonogashira and Glaser-type couplings. Its bench-stable nature and compatibility with common protecting group strategies make it a practical choice for constructing complex aromatic scaffolds in medicinal chemistry and materials synthesis.

Synthesis

  • Route1
    • null|null
      536-74-3
    • In-stock
      2-Bromobenzaldehyde|CS-D1759
      6630-33-7
    • ~98%
    • In-stock
      2-(Phenylethynyl)benzaldehyde|CS-0156581
      59046-72-9

    References

    • Yoshida, Kazuhiro; Nishii, Kana; Kano, Yuto; Wada, Shiro; Yanagisawa, Akira Journal of Organic Chemistry, 2014 , vol. 79, # 9 p. 4231 - 4239
  • Route2

    References

    • Wang, Shihua; Wang, Min; Wang, Lei; Wang, Bo; Li, Pinhua; Yang, Jin Tetrahedron, 2011 , vol. 67, # 26 p. 4800 - 4806
  • Route3

    References

    • Tokimizu, Yusuke; Ohta, Yusuke; Chiba, Hiroaki; Oishi, Shinya; Fujii, Nobutaka; Ohno, Hiroaki Tetrahedron, 2011 , vol. 67, # 29 p. 5168 - 5175

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

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Computational Chemistry Data

  • TPSA   17.07
  • LogP   2.8989
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   1

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