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CS-W001157 4
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4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine

  • CAS No. 869901-52-0

  • Cat. No. CS-0175750
  • Purity≥98%
  • MDL No.None

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

4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine|CS-0175750

Structure of 869901-52-0

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General Information

  • CAS No. 869901-52-0
  • Cat. No. CS-0175750
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₀H₁₄BNO₂
  • Molecular Weight 191.03
  • Synonym(s) Pyridine-4-boronic acid, neopentyl ester
  • SMILES CC1(COB(OC1)C2=CC=NC=C2)C

Description

4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine features a boronate ester group integrated with a pyridine heterocycle, enabling efficient cross-coupling reactions under mild conditions. The dimethyl-substituted dioxaborinane moiety enhances stability and moisture tolerance, while the electron-deficient pyridine ring facilitates selective functionalization in complex molecular architectures. This reagent streamlines the construction of biaryl systems in medicinal chemistry and materials science applications.

Application

4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine serves as a stable, bench-ready boronate building block for Suzuki-Miyaura cross-coupling reactions. Its sterically protected dioxaborinane moiety enhances air and moisture stability, enabling reliable coupling with aryl, heteroaryl, and vinyl halides. The pyridine core provides a versatile scaffold for constructing biologically relevant heterocycles, with excellent functional group tolerance and straightforward purification.

Synthesis

  • Route1
    • In-stock
      4-Pyridineboronic acid|CS-D1206
      1692-15-5
    • null|null
      126-30-7
    • ~99%
    • In-stock
      4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)pyridine|CS-0175750
      869901-52-0

    References

    • Maki, Toshikatsu; Ishihara, Kazuaki; Yamamoto, Hisashi Organic Letters, 2005 , vol. 7, # 22 p. 5043 - 5046 Title/Abstract Full Text View citing articles Show Details Maki, Toshikatsu; Ishihara, Kazuaki; Yamamoto, Hisashi Tetrahedron, 2007 , vol. 63, # 35 p. 8645 - 8657

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-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

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Computational Chemistry Data

  • TPSA   31.35
  • LogP   0.8498
  • H_Acceptors   3
  • H_Donors   0
  • Rotatable_Bonds   1

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