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CS-W001157 4
Total: USD 88.00

2-Hydroxy-5-nitropyridine

  • CAS No. 5418-51-9

  • Cat. No. CS-W016470
  • Purity≥98%
  • MDL No.MFCD00006276

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

2-Hydroxy-5-nitropyridine|CS-W016470

Structure of 5418-51-9

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General Information

  • CAS No. 5418-51-9
  • Cat. No. CS-W016470
  • Purity ≥98%
  • MDL No. MFCD00006276
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₄N₂O₃
  • Molecular Weight 140.10
  • Synonym(s) 5-nitropyridin-2(3H)-one; 2-Hydroxy-5-nitropyridine
  • SMILES O=[N+](C1=CN=C(O)C=C1)[O-]

Description

2-Hydroxy-5-nitropyridine features a strategically positioned hydroxyl group flanked by a nitro substituent on the pyridine ring, enabling dual hydrogen-bonding interactions. This electronic configuration enhances its utility as a ligand in transition metal catalysis and as a building block in bioactive heterocycle synthesis under standard conditions.

Application

2-Hydroxy-5-nitropyridine serves as a versatile building block in heterocyclic synthesis, enabling direct functionalization at the C2 and C5 positions due to orthogonal reactivity of the hydroxyl and nitro groups. Its bench-stable nature facilitates handling and purification, while the electron-withdrawing nitro group enhances electrophilic substitution efficiency. This compound functions as a key intermediate in the construction of bioactive scaffolds and pharmaceutical precursors through established coupling and cyclization protocols.

Synthesis

  • Route1

    References

    • Kokars; Yanishevskii; Kampars Chemistry of Heterocyclic Compounds, 2002 , vol. 38, # 7 p. 805 - 809
  • Route2
    • In-stock
      N,N-Dimethyl-5-nitropyridin-2-amine|CS-0089813
      2554-75-8
    • ~23%
    • In-stock
      2-Hydroxy-5-nitropyridine|CS-W016470
      5418-51-9
    • null|null
      113509-58-3

    References

    • Journal of Organic Chemistry, , vol. 53, # 9 p. 1887 - 1894
  • Route3

    References

    • Journal of the American Chemical Society, , vol. 77, p. 1045

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 : P261-P264-P271-P280-P302+P352-P304+P340-P362-P405-P501

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Computational Chemistry Data

  • TPSA   76.26
  • LogP   0.6954
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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