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(4-Methylpyridin-2-yl)boronic acid

  • CAS No. 372963-48-9

  • Cat. No. CS-0175834
  • Purity≥95%
  • MDL No.MFCD03093330

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

(4-Methylpyridin-2-yl)boronic acid|CS-0175834

Structure of 372963-48-9

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General Information

  • CAS No. 372963-48-9
  • Cat. No. CS-0175834
  • Purity ≥95%
  • MDL No. MFCD03093330
  • Storage -20°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₈BNO₂
  • Molecular Weight 136.94
  • Synonym(s) 4-Methylpyridine-2-boronic acid
  • SMILES CC1=CC(B(O)O)=NC=C1

Description

This boronate moiety integrates a 4-methylpyridin-2-yl group, offering enhanced stability and solubility in polar solvents. The electron-rich pyridine ring facilitates efficient coupling in Suzuki-Miyaura reactions, while the methyl substituent provides steric and electronic modulation. Bench-stable under standard conditions, it enables reliable cross-coupling without requiring inert atmosphere handling.

Application

(4-Methylpyridin-2-yl)boronic acid serves as a versatile building block in Suzuki-Miyaura cross-coupling reactions, enabling efficient C–C bond formation under mild conditions. Its pyridyl boronic acid functionality exhibits excellent bench stability, tolerates a range of functional groups, and facilitates the construction of biologically relevant heterocyclic scaffolds. The methyl substituent enhances solubility and modulates electronic properties, improving reactivity in diverse synthetic contexts.

Synthesis

  • Route1

    References

    • US2010/41714 A1, ; Page/Page column 17-18 ; US 20100041714 A1

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
Precautionary Statements : P264-P270-P301+P310-P330-P501

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Computational Chemistry Data

  • TPSA   53.35
  • LogP   -0.93018
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   1

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