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CS-W001157 4
Total: USD 88.00

((4-Iodophenyl)ethynyl)trimethylsilane

  • CAS No. 134856-58-9

  • Cat. No. CS-0041095
  • Purity≥95%
  • MDL No.MFCD04974026

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

((4-Iodophenyl)ethynyl)trimethylsilane|CS-0041095

Structure of 134856-58-9

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General Information

  • CAS No. 134856-58-9
  • Cat. No. CS-0041095
  • Purity ≥95%
  • MDL No. MFCD04974026
  • Storage 4°C, protect from light
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₃ISi
  • Molecular Weight 300.21
  • Synonym(s) TRIMETHYLSILYL ETHYNYL-4-IODOBENZENE
  • SMILES C[Si](C#CC1=CC=C(I)C=C1)(C)C

Description

This boronate moiety integrates a para-iodophenyl group with a trimethylsilyl-protected alkyne, enabling efficient copper-catalyzed coupling under standard conditions. The silyl-protected alkyne offers enhanced stability and moisture tolerance, simplifying handling in synthetic workflows.

Application

((4-Iodophenyl)ethynyl)trimethylsilane serves as a versatile building block in palladium-catalyzed coupling reactions, enabling efficient access to conjugated aryl alkynes. The trimethylsilyl group provides excellent bench stability and facilitates purification, while the iodide functions as a reliable coupling handle in Sonogashira, Suzuki-Miyaura, and Stille reactions. Its compatibility with diverse functional groups makes it a practical choice for constructing complex molecular architectures in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Aujard; Baltaze; Baudin; Cogne; Ferrage; Jullien; Perez; Prevost; Lin Mao Qian; Ruel Journal of the American Chemical Society, 2001 , vol. 123, # 34 p. 8177 - 8188
  • Route2

    References

    • Blakskjaer, Peter; Gothelf, Kurt V. Organic and Biomolecular Chemistry, 2006 , vol. 4, # 18 p. 3442 - 3447
  • Route3
    • In-stock
      1,4-Diiodobenzene|CS-W007412
      624-38-4
    • null|null
      1066-54-2
    • ~54%
    • In-stock
      ((4-Iodophenyl)ethynyl)trimethylsilane|CS-0041095
      134856-58-9

    References

    • Yao, Yuxing; Tour, James M. Journal of Organic Chemistry, 1999 , vol. 64, # 6 p. 1968 - 1971

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H319-H413
Precautionary Statements : P264-P273-P280-P501

Quality Control

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Computational Chemistry Data

  • TPSA   0
  • LogP   3.5201
  • H_Acceptors   0
  • H_Donors   0
  • Rotatable_Bonds   0

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