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2-Hydroxy-5-nitrobenzonitrile

  • CAS No. 39835-09-1

  • Cat. No. CS-0113070
  • Purity≥98%
  • MDL No.MFCD00234258

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

2-Hydroxy-5-nitrobenzonitrile|CS-0113070

Structure of 39835-09-1

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General Information

  • CAS No. 39835-09-1
  • Cat. No. CS-0113070
  • Purity ≥98%
  • MDL No. MFCD00234258
  • Storage RT, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₄N₂O₃
  • Molecular Weight 164.12
  • Synonym(s) 2-cyano-4-nitrophenol
  • SMILES N#CC1=CC([N+]([O-])=O)=CC=C1O

Description

2-Hydroxy-5-nitrobenzonitrile features a hydroxyl group ortho to a nitro substituent and flanked by a cyano group, enabling unique coordination behavior in metal complexation. This electron-deficient aromatic scaffold offers enhanced solubility in polar solvents and stability under standard bench conditions, facilitating use in synthetic transformations and ligand design.

Application

2-Hydroxy-5-nitrobenzonitrile serves as a versatile building block in medicinal chemistry and agrochemical synthesis, enabling efficient access to substituted benzimidazoles and other heterocyclic scaffolds. Its ortho-hydroxyl and nitro groups provide complementary reactivity for coupling reactions and cyclization protocols. The molecule exhibits good bench stability and facilitates straightforward purification, making it well-suited for iterative synthetic workflows.

Synthesis

  • Route1

    References

    • Makosza, Mieczyslaw; Sienkiewicz, Krzysztof Journal of Organic Chemistry, 1998 , vol. 63, # 13 p. 4199 - 4208
  • Route2

    References

    • Zamri; Schalk; Pattus; Abdallah Bioorganic and Medicinal Chemistry Letters, 2003 , vol. 13, # 6 p. 1147 - 1150
  • Route3

    References

    • Makosza, Mieczyslaw; Sienkiewicz, Krzysztof Journal of Organic Chemistry, 1998 , vol. 63, # 13 p. 4199 - 4208

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-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   87.16
  • LogP   1.17208
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   1

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