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CS-W001157 4
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3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl);isonicotinonitrile

  • CAS No. 878194-91-3

  • Cat. No. CS-0130357
  • Purity≥95%
  • MDL No.None

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

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl);isonicotinonitrile|CS-0130357

Structure of 878194-91-3

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General Information

  • CAS No. 878194-91-3
  • Cat. No. CS-0130357
  • Purity ≥95%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₅BN₂O₂
  • Molecular Weight 230.07
  • Synonym(s) 4-Cyanopyridine-3-Boronic Acid Pinacol Ester
  • SMILES N#CC1=CC=NC=C1B2OC(C)(C)C(C)(C)O2

Description

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isonicotinonitrile features a boronate ester group paired with a nitrile-substituted pyridine core. This combination enables efficient Suzuki-Miyaura coupling under mild conditions, delivering aryl nitriles with high functional group tolerance and minimal byproduct formation. The tetramethyl dioxaborolane moiety enhances stability and shelf life, while the para-nitrile position facilitates downstream transformations.

Application

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isonicotinonitrile serves as a versatile boronate building block in palladium-catalyzed cross-coupling reactions. Its nitrile group provides orthogonal functionality for downstream transformations, while the sterically protected boronate moiety ensures excellent stability and compatibility with diverse reaction conditions. Ideal for constructing substituted heterocycles and functionalized aryl scaffolds in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Cailly, Thomas; Fabis, Frederic; Bouillon, Alexandre; Lemaitre, Stephane; Sopkova, Jana; De Santos, Olivieira; Rault, Sylvain Synlett, 2006 , # 1 art. no. G33905ST, p. 53 - 56
  • Route2

    References

    • Cailly, Thomas; Lemaitre, Stephane; Fabis, Frederic; Rault, Sylvain Synthesis, 2007 , # 20 p. 3247 - 3251
  • Route3

    References

    • Synlett, , # 1 art. no. G33905ST, p. 53 - 56

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H319
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   55.14
  • LogP   1.25248
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   1

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