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3-Bromo-6-methyl-5-nitro-1H-pyridin-2-one

  • CAS No. 874493-25-1

  • Cat. No. CS-0037558
  • Purity≥98%
  • MDL No.None

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

3-Bromo-6-methyl-5-nitro-1H-pyridin-2-one|CS-0037558

Structure of 874493-25-1

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General Information

  • CAS No. 874493-25-1
  • Cat. No. CS-0037558
  • Purity ≥98%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₅BrN₂O₃
  • Molecular Weight 233.02
  • Synonym(s) 3-Bromo-6-methyl-5-nitropyridin-2-ol
  • SMILES CC1=NC(=C(C=C1[N+](=O)[O-])Br)O

Description

3-Bromo-6-methyl-5-nitro-1H-pyridin-2-one is a heterocyclic building block featuring a bromine at C3, a methyl group at C6, and a nitro substituent at C5 on the pyridin-2-one core. This electron-deficient scaffold enables direct coupling in cross-coupling reactions and supports derivatization under mild conditions. The molecule exhibits bench-stable handling characteristics and integrates readily into synthetic sequences targeting bioactive compounds.

Application

3-Bromo-6-methyl-5-nitro-1H-pyridin-2-one serves as a versatile building block in heterocyclic synthesis, enabling palladium-catalyzed cross-coupling reactions due to its bromo functionality. The nitro group enhances electrophilicity at C5, facilitating nucleophilic substitution and subsequent transformations. Its methyl substituent provides steric and electronic modulation, while the pyridin-2-one core offers stability and compatibility with diverse reaction conditions. Ideal for medicinal chemistry applications requiring functionalized pyridone scaffolds.

Synthesis

  • Route1

    References

    • SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED Patent: WO2008/101682 A2, 2008 ; Location in patent: Page/Page column 42 ;
  • Route2

    References

    • Brown; Burke Journal of the American Chemical Society, 1955 , vol. 77, p. 6053
  • Route3

    References

    • Parker; Shive Journal of the American Chemical Society, 1947 , vol. 69, p. 63,66

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-H320-H335
Precautionary Statements : P261-P280-P302+P352

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Computational Chemistry Data

  • TPSA   76.26
  • LogP   1.76632
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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