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CS-W001157 4
Total: USD 88.00

2-(Trimethylsilyl)phenol

  • CAS No. 15288-53-6

  • Cat. No. CS-0243969
  • Purity≥97%
  • MDL No.MFCD09909727

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

2-(Trimethylsilyl)phenol|CS-0243969

Structure of 15288-53-6

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General Information

  • CAS No. 15288-53-6
  • Cat. No. CS-0243969
  • Purity ≥97%
  • MDL No. MFCD09909727
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₄OSi
  • Molecular Weight None
  • Synonym(s) Phenol, o-(trimethylsilyl)-
  • SMILES OC1=CC=CC=C1[Si](C)(C)C

Description

2-(Trimethylsilyl)phenol serves as a stable, moisture-tolerant phenolic building block featuring a bulky trimethylsilyl group that enhances solubility and protects the hydroxyl functionality. This silyl ether derivative facilitates selective transformations in synthetic sequences and integrates seamlessly into complex molecular architectures under standard conditions.

Application

2-(Trimethylsilyl)phenol serves as a stable, bench-friendly phenolic building block enabling regioselective functionalization via silyl group activation. Its ortho-trimethylsilyl moiety facilitates directed metalation and acts as a temporary protecting group for hydroxyl functionality during multi-step syntheses. The compound exhibits excellent compatibility with common coupling reactions and provides straightforward desilylation under mild basic conditions, making it valuable for constructing complex aromatic scaffolds in medicinal chemistry and materials synthesis.

Synthesis

  • Route1
    • Trimethyl(2-((trimethylsilyl)oxy)phenyl)silane|CS-0521793
      18036-83-4
    • ~94%
    • In-stock
      2-(Trimethylsilyl)phenol|CS-0243969
      15288-53-6

    References

    • Atkinson, Darcy J.; Sperry, Jonathan; Brimble, Margaret A. Synthesis, 2010 , # 6 p. 911 - 913
  • Route2
    • (2-Bromophenoxy)trimethylsilane|CS-1156282
      36601-47-5
    • ~89%
    • In-stock
      2-(Trimethylsilyl)phenol|CS-0243969
      15288-53-6

    References

    • Michel, Boris; Greaney, Michael F. Organic Letters, 2014 , vol. 16, # 10 p. 2684 - 2687
  • Route3
    • null|null
      265671-60-1
    • ~49%
    • In-stock
      2-(Trimethylsilyl)phenol|CS-0243969
      15288-53-6
    • null|null
      90-43-7

    References

    • Studer, Armido; Bossart, Martin; Vasella, Tomaso Organic Letters, 2000 , vol. 2, # 7 p. 985 - 988

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05
Signal Word : Danger
UN#: 3265
Class : 8
Packing Group : Ⅲ
Hazard Statements : H314
Precautionary Statements : P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P363-P405-P501

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Computational Chemistry Data

  • TPSA   20.23
  • LogP   1.9374
  • H_Acceptors   1
  • H_Donors   1
  • Rotatable_Bonds   1

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