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3-Nitro-5-(trifluoromethyl)pyridin-2(1H)-one

  • CAS No. 33252-64-1

  • Cat. No. CS-0157385
  • Purity≥98%
  • MDL No.MFCD00153193

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

3-Nitro-5-(trifluoromethyl)pyridin-2(1H)-one|CS-0157385

Structure of 33252-64-1

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General Information

  • CAS No. 33252-64-1
  • Cat. No. CS-0157385
  • Purity ≥98%
  • MDL No. MFCD00153193
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₆H₃F₃N₂O₃
  • Molecular Weight 208.09
  • Synonym(s) 2-Hydroxy-3-nitro-5-(trifluoromethyl)pyridine
  • SMILES C1=C(C=NC(=C1[N+](=O)[O-])O)C(F)(F)F

Description

3-Nitro-5-(trifluoromethyl)pyridin-2(1H)-one features a strategically positioned nitro group and trifluoromethyl substituent on a pyridinone scaffold, delivering enhanced electron deficiency and metabolic stability. This combination enables efficient coupling in late-stage functionalization and transition metal-catalyzed transformations. The compound exhibits robust bench stability and solubility in common organic solvents, facilitating its use in synthetic medicinal chemistry and materials development workflows.

Application

3-Nitro-5-(trifluoromethyl)pyridin-2(1H)-one serves as a versatile building block in medicinal chemistry, enabling direct functionalization at the C3 position via nucleophilic substitution or metal-catalyzed coupling. The electron-deficient pyridinone core exhibits enhanced reactivity toward amines and thiols, while the trifluoromethyl group imparts metabolic stability and modulates lipophilicity. Bench-stable and readily purified by recrystallization, it functions efficiently in late-stage diversification of heterocyclic scaffolds.

Synthesis

  • Route1

    References

    • Respiratorius AB Patent: WO2009/7418 A1, 2009 ; Location in patent: Page/Page column 23 ;
  • Route2

    References

    • Sapegin, Alexander V.; Kalinin, Stanislav A.; Smirnov, Alexey V.; Dorogov, Mikhail V.; Krasavin, Mikhail Tetrahedron, 2014 , vol. 70, # 5 p. 1077 - 1083
  • Route3

    References

    • Tetrahedron, , vol. 70, # 5 p. 1077 - 1083

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-H312-H315-H319-H332-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   76.26
  • LogP   1.7142
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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