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CS-W001157 4
Total: USD 88.00

4-Ethynyl-N,N-diphenylaniline

  • CAS No. 205877-26-5

  • Cat. No. CS-0146642
  • Purity≥95%
  • MDL No.MFCD09030769

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

4-Ethynyl-N,N-diphenylaniline|CS-0146642

Structure of 205877-26-5

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General Information

  • CAS No. 205877-26-5
  • Cat. No. CS-0146642
  • Purity ≥95%
  • MDL No. MFCD09030769
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₂₀H₁₅N
  • Molecular Weight 269.34
  • Synonym(s) 4-Diphenylaminophenylacetylene
  • SMILES C#CC1=CC=C(N(C2=CC=CC=C2)C3=CC=CC=C3)C=C1

Description

4-Ethynyl-N,N-diphenylaniline integrates a terminal alkyne group with a diphenylamine scaffold, enabling efficient copper-catalyzed coupling reactions. This bench-stable, moisture-tolerant building block facilitates the synthesis of conjugated molecular architectures in materials science and chemical biology applications.

Application

4-Ethynyl-N,N-diphenylaniline serves as a versatile building block in transition-metal-catalyzed coupling reactions, enabling efficient access to conjugated enynes and aryl-substituted alkynes. Its terminal alkyne functionality exhibits high reactivity in Sonogashira and Glaser-type couplings, while the diphenylamino group provides electronic stabilization and enhanced solubility. The compound demonstrates excellent bench stability and facilitates straightforward purification, making it well-suited for applications in organic synthesis, materials science, and the construction of complex heterocyclic scaffolds.

Synthesis

  • Route1
    • null|null
      205877-25-4
    • ~93%
    • In-stock
      4-Ethynyl-N,N-diphenylaniline|CS-0146642
      205877-26-5

    References

    • Fang, Jing-Kun; An, De-Lie; Wakamatsu, Kan; Ishikawa, Takeharu; Iwanaga, Tetsuo; Toyota, Shinji; Matsuo, Daisuke; Orita, Akihiro; Otera, Junzo Tetrahedron Letters, 2010 , vol. 51, # 6 p. 917 - 920
  • Route2
    • null|null
      1223510-91-5
    • ~94%
    • In-stock
      4-Ethynyl-N,N-diphenylaniline|CS-0146642
      205877-26-5

    References

    • Grelaud, Guillaume; Cifuentes, Marie P.; Schwich, Torsten; Argouarch, Gilles; Petrie, Simon; Stranger, Rob; Paul, Frederic; Humphrey, Mark G. European Journal of Inorganic Chemistry, 2012 , # 1 p. 65 - 75
  • Route3

    References

    • Journal of Organic Chemistry, , vol. 70, # 4 p. 1134 - 1146

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-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   3.24
  • LogP   5.1377
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   3

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