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CS-W001157 4
Total: USD 88.00

Cyclopropyl(trimethylsilyl)acetylene

  • CAS No. 81166-84-9

  • Cat. No. CS-M3250
  • Purity≥97%
  • MDL No.MFCD00671355

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

Cyclopropyl(trimethylsilyl)acetylene|CS-M3250

Structure of 81166-84-9

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General Information

  • CAS No. 81166-84-9
  • Cat. No. CS-M3250
  • Purity ≥97%
  • MDL No. MFCD00671355
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₁₄Si
  • Molecular Weight 138.28
  • Synonym(s) Silane,(cyclopropylethynyl)trimethyl-(9CI); (Cyclopropylethynyl)(trimethyl)silane
  • SMILES C[Si](C)(C)C#CC1CC1

Description

Cyclopropyl(trimethylsilyl)acetylene is a bench-stable, moisture-tolerant alkyne reagent featuring a sterically protected silyl group and a strained cyclopropyl ring. This combination enables efficient copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions with high regioselectivity. The molecule integrates seamlessly into bioconjugation workflows and complex molecular scaffolds where stability and predictable reactivity are essential.

Application

Cyclopropyl(trimethylsilyl)acetylene serves as a valuable building block in transition-metal-catalyzed coupling reactions, enabling efficient access to substituted alkynes under mild conditions. Its silyl group provides enhanced stability and facilitates selective deprotection, while the cyclopropyl moiety imparts unique steric and electronic properties beneficial for constructing complex molecular architectures. The compound exhibits excellent bench stability and compatibility with a range of functional groups, making it well-suited for iterative synthesis in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • null|null
      75-77-4
    • null|null
      6746-94-7
    • ~81%
    • In-stock
      Cyclopropyl(trimethylsilyl)acetylene|CS-M3250
      81166-84-9

    References

    • Kozhushkov, Sergei I.; Wagner-Gillen, Karsten; Khlebnikov, Alexander F.; Demeijere, Armin Synthesis, 2010 , # 23 art. no. T17810SS, p. 3967 - 3973
  • Route2
    • null|null
      77113-48-5
    • ~82%
    • In-stock
      Cyclopropyl(trimethylsilyl)acetylene|CS-M3250
      81166-84-9

    References

    • Militzer; Schomenauer; Otte; Puls; Hain; Brase; De Meijere Synthesis, 1993 , # 10 p. 998 - 1012
  • Route3
    • null|null
      75-77-4
    • 1-Chloro-1-(1,2,2-trichloroethenyl)cyclopropane|CS-0745822
      82979-27-9
    • ~7%
    • In-stock
      Cyclopropyl(trimethylsilyl)acetylene|CS-M3250
      81166-84-9
    • null|null
      83662-48-0

    References

    • Chemische Berichte, , vol. 119, # 10 p. 2995 - 3026

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS02
Signal Word : Danger
UN#: 1993
Class : 3
Packing Group : Ⅲ
Hazard Statements : H226-H315-H319-H335
Precautionary Statements : P210-P233-P240-P241-P242-P243-P260-P261-P264-P271-P280-P302+P352-P304+P340-P362-P370+P378-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   0
  • LogP   2.2772
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   0

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