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CS-W001157 4
Total: USD 88.00

2-Ethynyl-naphthalene

  • CAS No. 2949-26-0

  • Cat. No. CS-W005234
  • Purity≥96%
  • MDL No.None

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

2-Ethynyl-naphthalene|CS-W005234

Structure of 2949-26-0

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General Information

  • CAS No. 2949-26-0
  • Cat. No. CS-W005234
  • Purity ≥96%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₈
  • Molecular Weight 152.19
  • Synonym(s) 2-Ethynylnaphthalene
  • SMILES C#CC1=CC=C2C=CC=CC2=C1

Description

2-Ethynyl-naphthalene features a terminal alkyne group appended to the naphthalene core, enabling efficient copper-catalyzed coupling reactions. This structure delivers high reactivity in click chemistry protocols while maintaining bench-stable handling under standard conditions. The extended aromatic system enhances π-conjugation, ideal for constructing complex molecular architectures in synthetic and materials applications.

Application

2-Ethynyl-naphthalene serves as a versatile building block in transition-metal-catalyzed coupling reactions, enabling efficient access to conjugated biaryls and polycyclic architectures. Its terminal alkyne functionality exhibits high compatibility with Sonogashira, Glaser, and Cadiot-Chodkiewicz protocols, facilitating the construction of extended π-systems. The molecule demonstrates excellent bench stability and is readily purified by column chromatography, making it well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • null|null
      40231-00-3
    • ~98%
    • In-stock
      2-Ethynyl-naphthalene|CS-W005234
      2949-26-0

    References

    • Benanti, Travis L.; Saejueng, Pranorm; Venkataraman Chemical Communications, 2007 , # 7 p. 692 - 694
  • Route2
    • null|null
      218902-65-9
    • ~91%
    • In-stock
      2-Ethynyl-naphthalene|CS-W005234
      2949-26-0

    References

    • Zhao, Ming; Kuang, Chunxiang; Yang, Qing; Cheng, Xuezhi Tetrahedron Letters, 2011 , vol. 52, # 9 p. 992 - 994
  • Route3
    • null|null
      90965-06-3
    • In-stock
      2-Naphthaldehyde|CS-D1121
      66-99-9
    • ~70%
    • In-stock
      2-Ethynyl-naphthalene|CS-W005234
      2949-26-0

    References

    • Baxendale, Ian R.; Ley, Steven V.; Mansfield, Andrew C.; Smith, Christopher D. Angewandte Chemie, International Edition, 2009 , vol. 48, p. 4017 - 4021 Angewandte Chemie, 2009 , vol. 121, p. 4077 - 4081

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+H312+H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P501

Quality Control

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Computational Chemistry Data

  • TPSA   0
  • LogP   2.8211
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   0

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