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4,4,5,5-Tetramethyl-2-(4-((trifluoromethyl)thio)phenyl)-1,3,2-dioxaborolane

  • CAS No. 1005206-25-6

  • Cat. No. CS-0143891
  • Purity≥97%
  • MDL No.MFCD11042448

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

4,4,5,5-Tetramethyl-2-(4-((trifluoromethyl)thio)phenyl)-1,3,2-dioxaborolane|CS-0143891

Structure of 1005206-25-6

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General Information

  • CAS No. 1005206-25-6
  • Cat. No. CS-0143891
  • Purity ≥97%
  • MDL No. MFCD11042448
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₃H₁₆BF₃O₂S
  • Molecular Weight 304.14
  • Synonym(s) Trifluoromethylthio-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzene
  • SMILES FC(F)(F)SC1=CC=C(B2OC(C)(C)C(C)(C)O2)C=C1

Description

This boronate ester features a trifluoromethylthio-substituted phenyl ring, enhancing electronic modulation and stability. The tetramethyl-substituted dioxaborolane core provides excellent shelf life and reactivity in Suzuki-Miyaura cross-coupling reactions under standard conditions.

Application

4,4,5,5-Tetramethyl-2-(4-((trifluoromethyl)thio)phenyl)-1,3,2-dioxaborolane serves as a stable, bench-ready boronate building block for palladium-catalyzed cross-coupling reactions. Its trifluoromethylthio-substituted aryl group enables efficient Suzuki-Miyaura coupling with diverse electrophiles, offering enhanced metabolic stability and lipophilicity in medicinal chemistry applications. The sterically protected dioxaborolane core ensures high chemical stability, minimal protodeboronation, and straightforward purification by flash chromatography or crystallization.

Synthesis

  • Route1

    References

    • US2010/69381 A1, ; Page/Page column 71 ;
  • Route2

    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-H413
Precautionary Statements : P264-P270-P273-P330

Quality Control

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Computational Chemistry Data

  • TPSA   18.46
  • LogP   3.5977
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   2

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