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CS-W001157 4
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5-Fluoro-3-nitropyridin-2(1H)-one

  • CAS No. 136888-20-5

  • Cat. No. CS-W022382
  • Purity≥98%
  • MDL No.MFCD05662412

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

5-Fluoro-3-nitropyridin-2(1H)-one|CS-W022382

Structure of 136888-20-5

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General Information

  • CAS No. 136888-20-5
  • Cat. No. CS-W022382
  • Purity ≥98%
  • MDL No. MFCD05662412
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₃FN₂O₃
  • Molecular Weight 158.09
  • Synonym(s) 5-Fluoro-2-hydroxy-3-nitropyridine
  • SMILES O=C1C([N+]([O-])=O)=CC(F)=CN1

Description

5-Fluoro-3-nitropyridin-2(1H)-one features a fused heterocyclic core with orthogonal electron-withdrawing groups: a fluorine atom at the 5-position and a nitro group at the 3-position. This combination imparts strong electron deficiency, enhancing reactivity in nucleophilic substitution and enabling direct functionalization at the pyridone ring. The molecule exhibits bench-stable behavior under standard conditions, facilitating straightforward handling in synthetic workflows.

Application

5-Fluoro-3-nitropyridin-2(1H)-one serves as a versatile building block in medicinal chemistry, enabling the construction of nitrogen-containing heterocycles via palladium-catalyzed cross-coupling and nucleophilic substitution reactions. Its fluorine and nitro groups provide orthogonal reactivity for sequential functionalization, while the pyridinone core offers enhanced solubility and metabolic stability. The compound exhibits bench stability and facilitates straightforward purification, making it well-suited for iterative synthesis workflows in API development.

Synthesis

  • Route1

    References

    • ALMIRALL, S.A.; EASTWOOD, Paul Robert; GONZALEZ RODRIGUEZ, Jacob; GOMEZ CASTILLO, Elena; BACH TANA, Jordi Patent: WO2012/160030 A1, 2012 ; Location in patent: Page/Page column 66 ;
  • Route2

    References

    • Journal of Medicinal Chemistry, , vol. 56, # 4 p. 1656 - 1669
  • Route3

    References

    • Journal of Medicinal Chemistry, , vol. 56, # 4 p. 1656 - 1669

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P260-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   76
  • LogP   0.4222
  • H_Acceptors   3
  • H_Donors   1
  • Rotatable_Bonds   1

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