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

  • CAS No. 878194-93-5

  • Cat. No. CS-0099446
  • Purity≥98%
  • MDL No.MFCD08458477

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

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile|CS-0099446

Structure of 878194-93-5

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General Information

  • CAS No. 878194-93-5
  • Cat. No. CS-0099446
  • Purity ≥98%
  • MDL No. MFCD08458477
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₂H₁₅BN₂O₂
  • Molecular Weight 230.07
  • Synonym(s) 2-Cyanopyridine-3-Boronic Acid Pinacol Ester
  • SMILES N#CC1=NC=CC=C1B2OC(C)(C)C(C)(C)O2

Description

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile features a boronate ester group paired with a nitrile-bearing pyridine ring, enabling efficient Suzuki-Miyaura coupling under mild conditions. The tetramethyl-substituted dioxaborolane enhances stability and resistance to protodeboronation. This bifunctional scaffold integrates seamlessly into complex molecular architectures, particularly in pharmaceutical and agrochemical synthesis where traceless functionalization is critical.

Application

3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The picolinonitrile moiety provides a readily accessible handle for further functionalization, while the tetramethylboronate group ensures excellent stability, low toxicity, and compatibility with diverse reaction conditions. Its bench-stable nature and high reactivity facilitate efficient synthesis of biaryl and heteroaryl scaffolds in medicinal chemistry and materials science.

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 : GHS06
Signal Word : Danger
UN#: 2811
Class : 6.1
Packing Group : Ⅲ
Hazard Statements : H301-H315-H319-H335
Precautionary Statements : P233-P260-P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P340-P362-P403-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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