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CS-W001157 4
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1-(2-Hydroxy-3-nitrophenyl)ethan-1-one

  • CAS No. 28177-69-7

  • Cat. No. CS-0058405
  • Purity≥97%
  • MDL No.MFCD02683784

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

1-(2-Hydroxy-3-nitrophenyl)ethan-1-one|CS-0058405

Structure of 28177-69-7

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General Information

  • CAS No. 28177-69-7
  • Cat. No. CS-0058405
  • Purity ≥97%
  • MDL No. MFCD02683784
  • Storage RT, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₈H₇NO₄
  • Molecular Weight 181.15
  • Synonym(s) 1-(2-Hydroxy-3-nitrophenyl)ethanone
  • SMILES CC(C1=CC=CC([N+]([O-])=O)=C1O)=O

Description

1-(2-Hydroxy-3-nitrophenyl)ethan-1-one features a phenolic hydroxyl and nitro group ortho to the ketone, enabling intramolecular hydrogen bonding that enhances stability and influences reactivity in electrophilic substitution. This structural motif supports applications in synthetic intermediates for bioactive molecule development and metal chelation studies.

Application

1-(2-Hydroxy-3-nitrophenyl)ethan-1-one serves as a versatile building block in synthetic organic chemistry, enabling the construction of substituted quinoline and isoquinoline scaffolds through well-established cyclization protocols. The ortho-hydroxy nitroaryl ketone functionality facilitates efficient intramolecular reactions under mild conditions, offering excellent bench stability and straightforward purification. Its functional group tolerance supports further derivatization in medicinal chemistry and materials science applications.

Synthesis

  • Route1

    References

    • Cushman, Mark; Zhu, Helen; Geahlen, Robert L.; Kraker, Alan J. Journal of Medicinal Chemistry, 1994 , vol. 37, # 20 p. 3353 - 3362
  • Route2
    • 1-(5-Amino-2-hydroxy-3-nitrophenyl)ethanone|CS-0533004
      108129-55-1
    • ~91%
    • In-stock
      1-(2-Hydroxy-3-nitrophenyl)ethan-1-one|CS-0058405
      28177-69-7

    References

    • Cushman, Mark; Zhu, Helen; Geahlen, Robert L.; Kraker, Alan J. Journal of Medicinal Chemistry, 1994 , vol. 37, # 20 p. 3353 - 3362
  • Route3

    References

    • Huang; Fu-Chich; Campbell; Henry F.; Learn; Keith S. Patent: US5082849 A1, 1992 ; US 5082849 A

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

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