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1-(3-Hydroxy-2-nitrophenyl)ethanone

  • CAS No. 53967-72-9

  • Cat. No. CS-0042567
  • Molecule weight181.15
  • Purity≥98%
  • MDL No.MFCD06251784

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

1-(3-Hydroxy-2-nitrophenyl)ethanone|CS-0042567

Structure of 53967-72-9

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General Information

  • CAS No. 53967-72-9
  • Cat. No. CS-0042567
  • Purity ≥98%
  • MDL No. MFCD06251784
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇NO₄
  • Molecular Weight 181.15
  • Synonym(s) 3'-Hydroxy-2'-nitroacetophenone
  • SMILES CC(=O)C1=C(C(O)=CC=C1)[N+]([O-])=O

Description

1-(3-Hydroxy-2-nitrophenyl)ethanone features a phenolic hydroxyl group flanked by electron-deficient nitro and ketone functionalities, enabling direct participation in hydrogen bonding and metal coordination. This structural motif supports integration into chelating ligands and bioactive scaffolds, offering enhanced solubility and reactivity under standard conditions.

Application

1-(3-Hydroxy-2-nitrophenyl)ethanone serves as a versatile building block in synthetic organic chemistry, enabling efficient access to nitro-substituted heterocycles and functionalized aryl ketones. Its ortho-hydroxy and nitro groups facilitate intramolecular cyclization and directed metalation, while the acetyl functionality supports further derivatization via standard carbonyl reactions. The compound exhibits good bench stability and is amenable to purification by recrystallization or chromatography, making it well-suited for use in medicinal chemistry and process development workflows.

Synthesis

  • Route1

    References

    • Fuerstner, Alois; Domostoj, Mathias M.; Scheiper, Bodo Journal of the American Chemical Society, 2006 , vol. 128, # 24 p. 8087 - 8094
  • Route2

    References

    • Guo, Wei; Liu, Wenfeng; Zhu, Lingjian; Zhang, Yongqiang; Cheng, Pengfei; Dong, Guoqiang; Zhuang, Chunlin; Yao, Jianzhong; Sheng, Chunquan; Miao, Zhenyuan; Zhang, Wannian Chemistry and Biodiversity, 2011 , vol. 8, # 8 p. 1539 - 1549
  • Route3

    References

    • Spada; Casini Gazzetta Chimica Italiana, 1950 , vol. 80, p. 642,647

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

Quality Control

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Computational Chemistry Data

  • TPSA   80.44
  • LogP   1.503
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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