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CS-W001157 4
Total: USD 88.00

4-((Trimethylsilyl)ethynyl)phenol

  • CAS No. 88075-18-7

  • Cat. No. CS-0186856
  • Molecule weightNone
  • Purity≥95%
  • MDL No.MFCD20257321

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

4-((Trimethylsilyl)ethynyl)phenol|CS-0186856

Structure of 88075-18-7

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General Information

  • CAS No. 88075-18-7
  • Cat. No. CS-0186856
  • Purity ≥95%
  • MDL No. MFCD20257321
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₄OSi
  • Molecular Weight None
  • Synonym(s) Phenol, 4-[2-(trimethylsilyl)ethynyl]-
  • SMILES C[Si](C)(C)C#CC1=CC=C(C=C1)O

Description

4-((Trimethylsilyl)ethynyl)phenol features a terminal alkyne tethered to a phenolic ring, enabling efficient copper-catalyzed coupling reactions. The trimethylsilyl group provides enhanced stability and facilitates selective deprotection. This compound serves as a robust building block for conjugated systems in materials science and synthetic organic chemistry.

Application

4-((Trimethylsilyl)ethynyl)phenol serves as a versatile building block in transition-metal-catalyzed coupling reactions, enabling efficient access to substituted phenylacetylenes. The trimethylsilyl group provides enhanced stability and facilitates regioselective desilylation or cross-coupling under mild conditions. Its compatibility with palladium- and copper-mediated transformations makes it valuable for constructing conjugated systems and functionalized aromatic scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1
    • null|null
      540-38-5
    • null|null
      1066-54-2
    • ~99%
    • In-stock
      4-((Trimethylsilyl)ethynyl)phenol|CS-0186856
      88075-18-7

    References

    • Kwon, Jinsun; Kondaji, Gajulapati; Song, Sumi; Kim, Chorong; Lee, Kyeong; Kim, Won-Ki; Choi, Yongseok Bulletin of the Korean Chemical Society, 2013 , vol. 34, # 4 p. 1247 - 1249
  • Route2
    • null|null
      165825-13-8
    • ~87%
    • In-stock
      4-((Trimethylsilyl)ethynyl)phenol|CS-0186856
      88075-18-7

    References

    • Ladouceur, Sebastien; Soliman, Ahmed M.; Zysman-Colman, Eli Synthesis, 2011 , # 22 art. no. M79111SS, p. 3604 - 3611
  • Route3
    • null|null
      18803-26-4
    • null|null
      1066-54-2
    • ~85%
    • In-stock
      4-((Trimethylsilyl)ethynyl)phenol|CS-0186856
      88075-18-7

    References

    • Krause; Ligneau; Stark; Garbarg; Schwartz; Schunack Journal of Medicinal Chemistry, 1998 , vol. 41, # 21 p. 4171 - 4176

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

Quality Control

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Computational Chemistry Data

  • TPSA   20.23
  • LogP   2.6211
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   0

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