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CS-W001157 4
Total: USD 88.00

4,4'-(Ethyne-1,2-diyl)dibenzaldehyde

  • CAS No. 84907-55-1

  • Cat. No. CS-0110728
  • Molecule weightNone
  • Purity≥97%
  • MDL No.MFCD01573051

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

4,4'-(Ethyne-1,2-diyl)dibenzaldehyde|CS-0110728

Structure of 84907-55-1

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General Information

  • CAS No. 84907-55-1
  • Cat. No. CS-0110728
  • Purity ≥97%
  • MDL No. MFCD01573051
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₆H₁₀O₂
  • Molecular Weight None
  • Synonym(s) tolan-4,4'-dicarbaldehyde
  • SMILES O=CC1=CC=C(C=C1)C#CC2=CC=C(C=O)C=C2

Description

4,4'-(Ethyne-1,2-diyl)dibenzaldehyde features a rigid, linear alkyne bridge flanking two electron-deficient benzaldehyde groups, enabling efficient conjugation and precise spatial control. This structure facilitates reliable coupling in transition-metal-catalyzed reactions, particularly Sonogashira couplings, and supports the construction of extended π-systems for materials applications.

Application

4,4'-(Ethyne-1,2-diyl)dibenzaldehyde serves as a versatile diyne-linked aromatic aldehyde building block, enabling efficient access to conjugated π-systems via Sonogashira coupling and click chemistry. Its dual aldehyde functionality offers high compatibility with amine-based transformations, facilitating the construction of functionalized heterocycles and extended molecular architectures. Bench-stable and readily purified by recrystallization, it functions reliably in multi-step synthetic sequences requiring orthogonal reactivity.

Synthesis

  • Route1
    • 4-(Prop-1-yn-1-yl)benzaldehyde|CS-0775790
      172508-29-1
    • ~96%
    • In-stock
      4,4'-(Ethyne-1,2-diyl)dibenzaldehyde|CS-0110728
      84907-55-1

    References

    • The Regents of the University of Colorado, a body corporate; Zhang, Wei; Kuthanapillil, Jyothish; Wang, Qi Patent: US2013/261295 A1, 2013 ; Location in patent: Paragraph 0281; 0282 ;
  • Route2
    • null|null
      652974-14-6
    • ~83%
    • In-stock
      4,4'-(Ethyne-1,2-diyl)dibenzaldehyde|CS-0110728
      84907-55-1

    References

    • Zhang, Wei; Kraft, Stefan; Moore, Jeffrey S. Journal of the American Chemical Society, 2004 , vol. 126, # 1 p. 329 - 335
  • Route3
    • null|null
      75-20-7
    • In-stock
      4-Iodobenzaldehyde|CS-W002179
      15164-44-0
    • ~87%
    • In-stock
      4,4'-(Ethyne-1,2-diyl)dibenzaldehyde|CS-0110728
      84907-55-1

    References

    • Chuentragool, Padon; Vongnam, Kunnigar; Rashatasakhon, Paitoon; Sukwattanasinitt, Mongkol; Wacharasindhu, Sumrit Tetrahedron, 2011 , vol. 67, # 42 p. 8177 - 8182

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-P280-P302+P352

Quality Control

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Computational Chemistry Data

  • TPSA   34.14
  • LogP   2.7114
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   2

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