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CS-W001157 4
Total: USD 88.00

4-Cyanophenyl trifluoromethanesulfonate

  • CAS No. 66107-32-2

  • Cat. No. CS-0527342
  • Molecule weight251.18
  • Purity≥98%
  • MDL No.None

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

4-Cyanophenyl trifluoromethanesulfonate|CS-0527342

Structure of 66107-32-2

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General Information

  • CAS No. 66107-32-2
  • Cat. No. CS-0527342
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₄F₃NO₃S
  • Molecular Weight 251.18
  • Synonym(s) Methanesulfonic acid, 1,1,1-trifluoro-, 4-cyanophenyl ester
  • SMILES N#CC1=CC=C(C=C1)OS(=O)(C(F)(F)F)=O

Description

4-Cyanophenyl trifluoromethanesulfonate serves as a highly reactive arylating agent, featuring a triflate leaving group that enables efficient coupling under mild conditions. The para-cyano substituent enhances electrophilicity and stabilizes reaction intermediates. This bench-stable reagent integrates seamlessly into cross-coupling protocols for constructing functionalized biaryls in synthetic organic chemistry.

Application

4-Cyanophenyl trifluoromethanesulfonate serves as a robust arylating agent in palladium-catalyzed cross-coupling reactions, enabling efficient construction of biaryl scaffolds. Its triflate leaving group ensures high reactivity under standard conditions, while the electron-withdrawing cyano group enhances stability and facilitates purification. This compound functions reliably in Suzuki-Miyaura and Stille couplings, offering excellent functional group tolerance and bench stability for routine synthetic workflows.

Synthesis

  • Route1
    • null|null
      358-23-6
    • 4-Cyanophenol Febuxostat Impurity|CS-0213981
      767-00-0
    • ~99%
    • In-stock
      4-Cyanophenyl trifluoromethanesulfonate|CS-0527342
      66107-32-2

    References

    • Uchiyama, Masanobu; Kobayashi, Yuri; Furuyama, Taniyuki; Nakamura, Shinji; Kajihara, Yumiko; Miyoshi, Tomoko; Sakamoto, Takao; Kondo, Yoshinori; Morokuma, Keiji Journal of the American Chemical Society, 2008 , vol. 130, # 2 p. 472 - 480
  • Route2
    • In-stock
      N,N-Bis(trifluoromethylsulfonyl)aniline|CS-B0879
      37595-74-7
    • 4-Cyanophenol Febuxostat Impurity|CS-0213981
      767-00-0
    • ~91%
    • In-stock
      4-Cyanophenyl trifluoromethanesulfonate|CS-0527342
      66107-32-2

    References

    • Wentworth; Wentworth Jr.; Mansoor; Janda Organic letters, 2000 , vol. 2, # 4 p. 477 - 480
  • Route3
    • 4-Cyanophenol Febuxostat Impurity|CS-0213981
      767-00-0
    • null|null
      407-25-0
    • ~%
    • In-stock
      4-Cyanophenyl trifluoromethanesulfonate|CS-0527342
      66107-32-2

    References

    • Fuk Yee Kwong; Chi Wai Lai; Kin Shing Chan Journal of the American Chemical Society, 2001 , vol. 123, # 36 p. 8864 - 8865

Safety Information

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

Quality Control

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Computational Chemistry Data

  • TPSA   67.16
  • LogP   1.78668
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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