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CS-W001157 4
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4,4,5,5-Tetramethyl-2-(3,4,5-trifluorophenyl)-1,3,2-dioxaborolane

  • CAS No. 827614-70-0

  • Cat. No. CS-W000974
  • Purity≥98%
  • MDL No.MFCD05663885

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

4,4,5,5-Tetramethyl-2-(3,4,5-trifluorophenyl)-1,3,2-dioxaborolane|CS-W000974

Structure of 827614-70-0

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General Information

  • CAS No. 827614-70-0
  • Cat. No. CS-W000974
  • Purity ≥98%
  • MDL No. MFCD05663885
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₄BF₃O₂
  • Molecular Weight 258.05
  • Synonym(s) 3,4,5-Trifluorophenylboronic Acid Pinacol Ester
  • SMILES CC(C(C)(O1)C)(OB1C2=CC(F)=C(F)C(F)=C2)C

Description

This boronate ester features a trifluorophenyl group conjugated to a stable dioxaborolane core, enabling efficient cross-coupling under mild conditions. The tetramethyl substitution enhances shelf stability and solubility in organic media, while the electron-deficient aryl moiety facilitates rapid transmetalation. Ideal for Suzuki-Miyaura reactions requiring high functional group tolerance and predictable reactivity.

Application

4,4,5,5-Tetramethyl-2-(3,4,5-trifluorophenyl)-1,3,2-dioxaborolane serves as a stable, bench-ready boron building block for Suzuki-Miyaura cross-coupling reactions. Its trifluorophenyl moiety enables efficient coupling with aryl and heteroaryl halides, offering enhanced electron-withdrawing character for improved reactivity in challenging transformations. The tetramethyl substitution ensures high stability, minimal protodeboronation, and ease of purification, making it ideal for constructing complex pharmaceutical scaffolds and functionalized biaryls in iterative synthesis workflows.

Synthesis

  • Route1
    • In-stock
      2,3-Dimethylbutane-2,3-diol|CS-0015356
      76-09-5
    • null|null
      1338809-70-3
    • ~%
    • In-stock
      4,4,5,5-Tetramethyl-2-(3,4,5-trifluorophenyl)-1,3,2-dioxaborolane|CS-W000974
      827614-70-0

    References

    • Tetrahedron Letters, , vol. 54, # 2 p. 166 - 169
  • Route2
    • null|null
      61676-62-8
    • In-stock
      1-Bromo-3,4,5-trifluorobenzene|CS-W015081
      138526-69-9
    • ~84%
    • In-stock
      4,4,5,5-Tetramethyl-2-(3,4,5-trifluorophenyl)-1,3,2-dioxaborolane|CS-W000974
      827614-70-0

    References

    • Newby, James A.; Huck, Lena; Blaylock, D. Wayne; Witt, Paul M.; Ley, Steven V.; Browne, Duncan L. Chemistry - A European Journal, 2014 , vol. 20, # 1 p. 263 - 271
  • Route3

    References

    • Tetrahedron Letters, , vol. 54, # 2 p. 166 - 169

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   18.46
  • LogP   2.4031
  • H_Acceptors   2
  • H_Donors   0
  • Rotatable_Bonds   1

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