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

  • CAS No. 402718-29-0

  • Cat. No. CS-0041845
  • Purity≥97%
  • MDL No.MFCD07780755

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

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile|CS-0041845

Structure of 402718-29-0

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General Information

  • CAS No. 402718-29-0
  • Cat. No. CS-0041845
  • Purity ≥97%
  • MDL No. MFCD07780755
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₅BN₂O₂
  • Molecular Weight 230.08
  • Synonym(s) 3-Cyanopyridine-5-boronic Acid Pinacol Ester
  • SMILES CC1(C)OB(OC1(C)C)C1=CC(=CN=C1)C#N

Description

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile features a boronate ester group paired with a nitrile-substituted pyridine core. This combination enables efficient Suzuki-Miyaura coupling under standard conditions while maintaining bench stability and compatibility with diverse reaction environments. The tetramethyl substitution enhances hydrolytic resistance and operational robustness in synthetic workflows.

Application

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinonitrile serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The nitrile group provides enhanced solubility and metabolic stability, while the tetramethylborolane moiety ensures high reactivity and bench stability. Functions effectively in late-stage functionalization of heterocyclic scaffolds, enabling efficient access to substituted pyridine derivatives under mild reaction conditions.

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-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   55.14
  • LogP   1.25248
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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