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CS-W001157 4
Total: USD 88.00

4-(tert-Butyldimethylsilyloxy)-1-butyne

  • CAS No. 78592-82-2

  • Cat. No. CS-0181791
  • Purity≥98%
  • MDL No.MFCD03427046

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

4-(tert-Butyldimethylsilyloxy)-1-butyne|CS-0181791

Structure of 78592-82-2

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General Information

  • CAS No. 78592-82-2
  • Cat. No. CS-0181791
  • Purity ≥98%
  • MDL No. MFCD03427046
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₂₀OSi
  • Molecular Weight 184.35
  • Synonym(s) None
  • SMILES C#CCCO[Si](C)(C)C(C)(C)C

Application

4-(tert-Butyldimethylsilyloxy)-1-butyne serves as a stable, bench-ready building block for the synthesis of silyl-protected alkynyl intermediates. Its terminal alkyne functionality enables efficient copper-catalyzed coupling reactions, while the tert-butyldimethylsilyl (TBS) ether provides orthogonal protection compatible with standard deprotection protocols. The molecule exhibits excellent functional group tolerance and facilitates straightforward purification, making it ideal for use in complex molecule assembly and medicinal chemistry campaigns requiring reliable silyl-protected alkyne handles.

Synthesis

  • Route1
    • null|null
      18162-48-6
    • In-stock
      3-Butyn-1-ol|CS-W001947
      927-74-2
    • ~98%
    • In-stock
      4-(tert-Butyldimethylsilyloxy)-1-butyne|CS-0181791
      78592-82-2

    References

    • Yi, Jun; Lu, Xi; Sun, Yan-Yan; Xiao, Bin; Liu, Lei Angewandte Chemie - International Edition, 2013 , vol. 52, # 47 p. 12409 - 12413 Angew. Chem., 2013 , vol. 125, # 47 p. 12635 - 12639,5
  • Route2
    • null|null
      69739-34-0
    • In-stock
      3-Butyn-1-ol|CS-W001947
      927-74-2
    • ~95%
    • In-stock
      4-(tert-Butyldimethylsilyloxy)-1-butyne|CS-0181791
      78592-82-2

    References

    • Jones, Graham B.; Wright, Justin M.; Hynd, George; Wyatt, Justin K.; Warner, Philip M.; Huber, Robert S.; Li, Aiwen; Kilgore, Michael W.; Sticca, Robert P.; Pollenz, Richard S. Journal of Organic Chemistry, 2002 , vol. 67, # 16 p. 5727 - 5732
  • Route3
    • Imidazole Ondansetron Impurity|CS-0229601
      288-32-4
    • null|null
      18162-48-6
    • In-stock
      3-Butyn-1-ol|CS-W001947
      927-74-2
    • ~0%
    • In-stock
      4-(tert-Butyldimethylsilyloxy)-1-butyne|CS-0181791
      78592-82-2
    • null|null
      110519-15-8

    References

    • Bristol-Myers Squibb Company Patent: US5382592 A1, 1995 ; US 5382592 A

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS02,GHS07
Signal Word : Warning
UN#: 1993
Class : 3
Packing Group : Ⅲ
Hazard Statements : H226-H315-H319-H335
Precautionary Statements : P210-P233-P240-P241-P242-P243-P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P370+P378-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   9.23
  • LogP   3.0315
  • H_Acceptors   1
  • H_Donors   0
  • Rotatable_Bonds   3

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