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5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)benzonitrile

  • CAS No. 1220219-14-6

  • Cat. No. CS-B0681
  • Purity≥96%
  • MDL No.MFCD18383806

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

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)benzonitrile|CS-B0681

Structure of 1220219-14-6

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General Information

  • CAS No. 1220219-14-6
  • Cat. No. CS-B0681
  • Purity ≥96%
  • MDL No. MFCD18383806
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₄H₁₅BF₃NO₂
  • Molecular Weight 297.08
  • Synonym(s) Benzonitrile, 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)-
  • SMILES CC1(C)C(C)(C)OB(C2=CC=C(C(F)(F)F)C(C#N)=C2)O1

Description

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)benzonitrile features a boronate ester group paired with an electron-deficient trifluoromethyl nitrile moiety. This combination enables efficient Suzuki-Miyaura coupling under standard conditions, delivering arylated products with high functional group tolerance and excellent stability during storage and handling.

Application

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(trifluoromethyl)benzonitrile serves as a versatile boronate building block in palladium-catalyzed cross-coupling reactions. The tetramethylboronate group enables efficient Suzuki-Miyaura coupling under mild conditions, while the trifluoromethyl and nitrile functionalities provide enhanced metabolic stability and electronic modulation. Bench-stable and readily purified by flash chromatography, it facilitates the construction of complex biaryl scaffolds common in medicinal chemistry and materials science.

Safety Information

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GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319
Precautionary Statements : P264-P270-P280-P302+P352-P330-P362+P364-P501

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Computational Chemistry Data

  • TPSA   42.25
  • LogP   2.87628
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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