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CS-W001157 4
Total: USD 88.00

1-Ethynyladamantane

  • CAS No. 40430-66-8

  • Cat. No. CS-0052563
  • Purity≥97%
  • MDL No.None

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

1-Ethynyladamantane|CS-0052563

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General Information

  • CAS No. 40430-66-8
  • Cat. No. CS-0052563
  • Purity ≥97%
  • MDL No. None
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₆
  • Molecular Weight 160.26
  • Synonym(s) Adamantane,1-ethynyl- (7CI)
  • SMILES C#CC12C[C@H]3C[C@@H](C2)C[C@@H](C1)C3

Description

1-Ethynyladamantane offers a rigid, sterically encumbered alkyne handle ideal for copper-catalyzed click chemistry and bioconjugation. The adamantane scaffold imparts exceptional stability and lipophilicity, enhancing membrane permeability and metabolic resistance in probe design. This robust molecular framework integrates seamlessly into complex architectures without compromising structural integrity.

Application

1-Ethynyladamantane serves as a robust, bench-stable building block for CuAAC and Sonogashira coupling reactions. Its rigid adamantane scaffold imparts exceptional stability and enhances solubility in organic media, enabling efficient incorporation into complex molecular architectures. The terminal alkyne functionality facilitates reliable conjugation with azides and palladium-catalyzed cross-couplings, making it a valuable reagent for constructing functionalized scaffolds in medicinal chemistry and materials science.

Synthesis

  • Route1
    • null|null
      91800-98-5
    • ~91%
    • In-stock
      1-Ethynyladamantane|CS-0052563
      40430-66-8

    References

    • THE CURATORS OF THE UNIVERSITY OF MISSOURI; LEE, Jr., Mark Wayne; SEVRYUGINA, Yulia Patent: WO2013/82150 A1, 2013 ; Location in patent: Paragraph 0124 ;
  • Route2
    • null|null
      2094-74-8
    • null|null
      90965-06-3
    • ~77%
    • In-stock
      1-Ethynyladamantane|CS-0052563
      40430-66-8

    References

    • Wyeth Patent: US2007/27199 A1, 2007 ; Location in patent: Page/Page column 23 ; US 20070027199 A1
  • Route3

    References

    • Busch, Mark; Schlageter, Martin; Weingand, Daniel; Gehring, Timo Chemistry - A European Journal, 2009 , vol. 15, # 33 p. 8251 - 8258

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

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Computational Chemistry Data

  • TPSA   0
  • LogP   2.836
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   0

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