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(Bromoethynyl)triisopropylsilane

  • CAS No. 111409-79-1

  • Cat. No. CS-0148889
  • Purity≥97%
  • MDL No.MFCD11036302

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

(Bromoethynyl)triisopropylsilane|CS-0148889

Structure of 111409-79-1

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General Information

  • CAS No. 111409-79-1
  • Cat. No. CS-0148889
  • Purity ≥97%
  • MDL No. MFCD11036302
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₂₁BrSi
  • Molecular Weight 261.27
  • Synonym(s) Silane, (bromoethynyl)tris(1-methylethyl)-
  • SMILES CC([Si](C(C)C)(C#CBr)C(C)C)C

Description

(Bromoethynyl)triisopropylsilane features a bromoethynyl group tethered to a triisopropylsilyl moiety, offering a sterically shielded, bench-stable platform for transition-metal-catalyzed coupling reactions. The bulky silyl group enhances stability and solubility in organic media, enabling efficient incorporation into complex molecular architectures via palladium- or copper-mediated protocols.

Application

(Bromoethynyl)triisopropylsilane serves as a stable, bench-ready building block for Sonogashira coupling reactions. Its triisopropylsilyl-protected alkyne functionality enables efficient C–C bond formation under mild conditions, with excellent functional group tolerance and straightforward purification. The bromo substituent provides compatibility with palladium-catalyzed cross-coupling protocols, facilitating access to conjugated alkynes and complex molecular architectures in medicinal chemistry and materials synthesis.

Synthesis

  • Route1

    References

    • Nicolai, Stefano; Waser, Jerome Organic Letters, 2011 , vol. 13, # 23 p. 6324 - 6327

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05,GHS07
Signal Word : Danger
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H314-H335
Precautionary Statements : P260-P264-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P312-P363-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   0
  • LogP   4.5602
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   3

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