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CS-W001157 4
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5-Hydroxy-2-nitrobenzaldehyde

  • CAS No. 42454-06-8

  • Cat. No. CS-W001068
  • Purity≥95%
  • MDL No.MFCD00007332

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

5-Hydroxy-2-nitrobenzaldehyde|CS-W001068

Structure of 42454-06-8

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General Information

  • CAS No. 42454-06-8
  • Cat. No. CS-W001068
  • Purity ≥95%
  • MDL No. MFCD00007332
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅NO₄
  • Molecular Weight 167.12
  • Synonym(s) 5-Hydroxy-2-Nitro Benzaldehyde; 5-Hydroxy-2-nitrobenzaldehyde
  • SMILES O=CC1=CC(O)=CC=C1[N+]([O-])=O

Description

5-Hydroxy-2-nitrobenzaldehyde features a hydroxyl group flanked by a nitro substituent and aldehyde functionality, enabling its use in conjugated systems. This electron-deficient aromatic scaffold integrates readily into synthetic intermediates for dyes, pharmaceuticals, and ligands. The ortho-nitro group enhances reactivity toward nucleophiles while the phenolic OH supports metal coordination.

Application

5-Hydroxy-2-nitrobenzaldehyde serves as a versatile building block in synthetic organic chemistry, enabling direct access to substituted benzimidazoles and other heterocyclic scaffolds via condensation reactions. The ortho-nitro and hydroxyl groups provide strong directing effects for electrophilic substitution, while the aldehyde functionality facilitates facile coupling with amines and hydrazines. Bench-stable and compatible with standard purification methods, it functions effectively in multi-step syntheses requiring functional group tolerance and predictable reactivity.

Synthesis

  • Route1
    • 3-Hydroxybenzaldehyde Roxatidine Impurity|CS-0229483
      100-83-4
    • ~25%
    • In-stock
      5-Hydroxy-2-nitrobenzaldehyde|CS-W001068
      42454-06-8

    References

    • Essilor International (Compagnie Generale d'Optique) Patent: US5139707 A1, 1992 ;
  • Route2
    • null|null
      99306-51-1
    • ~67%
    • In-stock
      5-Hydroxy-2-nitrobenzaldehyde|CS-W001068
      42454-06-8

    References

    • Junsei Chemical Co., Ltd. Patent: US5847231 A1, 1998 ;
  • Route3
    • null|null
      454466-61-6
    • ~89%
    • In-stock
      5-Hydroxy-2-nitrobenzaldehyde|CS-W001068
      42454-06-8

    References

    • Katritzky, Alan R.; Wang, Zuoquan; Hall, C.Dennis; Ji, Yu; Akhmedov, Novruz G. Tetrahedron Letters, 2002 , vol. 43, # 18 p. 3449 - 3451

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-H412
Precautionary Statements : P261-P264-P271-P273-P280-P302+P352-P304+P340-P362-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   80.44
  • LogP   1.1129
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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