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CS-W001157 4
Total: USD 88.00

4-Methyl-2-(trimethylsilyl)phenyl trifluoromethanesulfonate

  • CAS No. 262373-15-9

  • Cat. No. CS-0182181
  • Purity≥95%
  • MDL No.MFCD10566914

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

4-Methyl-2-(trimethylsilyl)phenyl trifluoromethanesulfonate|CS-0182181

Structure of 262373-15-9

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General Information

  • CAS No. 262373-15-9
  • Cat. No. CS-0182181
  • Purity ≥95%
  • MDL No. MFCD10566914
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₅F₃O₃SSi
  • Molecular Weight 312.38
  • Synonym(s) Trifluoromethanesulfonic Acid 4-Methyl-2-(trimethylsilyl)phenyl Ester
  • SMILES O=S(C(F)(F)F)(OC1=CC=C(C)C=C1[Si](C)(C)C)=O

Description

4-Methyl-2-(trimethylsilyl)phenyl trifluoromethanesulfonate is a bench-stable silyl-protected aryl triflate featuring a methyl group at the ortho position. This configuration enhances regioselectivity in cross-coupling reactions, enabling efficient C–C bond formation under mild conditions. The trimethylsilyl moiety provides stability and facilitates subsequent desilylation.

Application

4-Methyl-2-(trimethylsilyl)phenyl trifluoromethanesulfonate serves as a stable, bench-ready aryl triflate building block for palladium-catalyzed cross-coupling reactions. Its ortho-trimethylsilyl group enhances solubility and modulates reactivity, while the triflate moiety enables reliable Suzuki, Stille, and Negishi coupling protocols. The molecule exhibits excellent functional group tolerance and facilitates efficient construction of substituted biaryls and complex heterocycles in medicinal chemistry workflows.

Synthesis

  • Route1
    • null|null
      358-23-6
    • In-stock
      2-Bromo-4-methylphenol|CS-W016869
      6627-55-0
    • null|null
      999-97-3
    • ~47%
    • In-stock
      4-Methyl-2-(trimethylsilyl)phenyl trifluoromethanesulfonate|CS-0182181
      262373-15-9

    References

    • Biju, Akkattu T.; Glorius, Frank Angewandte Chemie - International Edition, 2010 , vol. 49, # 50 p. 9761 - 9764

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05
Signal Word : Danger
UN#: 3265
Class : 8
Packing Group : Ⅱ
Hazard Statements : H290-H314
Precautionary Statements : P234-P260-P264-P280-P301+P330+P331-P304+P340-P363-P390-P405-P406-P501

Quality Control

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Computational Chemistry Data

  • TPSA   43.37
  • LogP   2.76862
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   3

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