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

  • CAS No. 1171891-35-2

  • Cat. No. CS-W006130
  • Purity≥95%
  • MDL No.MFCD11878279

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

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-ol|CS-W006130

Structure of 1171891-35-2

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General Information

  • CAS No. 1171891-35-2
  • Cat. No. CS-W006130
  • Purity ≥95%
  • MDL No. MFCD11878279
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₁₁H₁₆BNO₃
  • Molecular Weight 221.06
  • Synonym(s) 5-Hydroxypyridine-3-boronic acid pinacol ester
  • SMILES CC1(C)OB(OC1(C)C)C1=CN=CC(O)=C1

Description

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-ol features a boronate ester group conjugated to a pyridin-3-ol scaffold, enabling efficient Suzuki-Miyaura coupling under mild conditions. The tetramethyl-substituted dioxaborolane enhances stability and solubility in aqueous-organic mixtures, while the phenolic hydroxyl supports directional functionalization. This reagent streamlines the synthesis of biaryl heterocycles in medicinal chemistry and materials science.

Application

5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-ol serves as a versatile boronate building block for Suzuki-Miyaura coupling, enabling efficient construction of biaryl scaffolds under mild conditions. The pyridin-3-ol functionality provides orthogonal reactivity and enhanced solubility, while the tetramethyl-substituted dioxaborolane offers excellent stability and ease of purification. This compound facilitates rapid access to functionalized heterocycles in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Journal of Medicinal Chemistry, , vol. 51, # 22 p. 7099 - 7110

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   51.58
  • LogP   1.0864
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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