Cas no 1260785-45-2 (1-(4-Hydroxy-3-methoxy-2-nitrophenyl)ethanone)

1-(4-Hydroxy-3-methoxy-2-nitrophenyl)ethanone is a nitro-substituted aromatic ketone with a molecular formula of C9H9NO5. This compound features a hydroxy and methoxy group adjacent to a nitro substituent, contributing to its unique reactivity and potential applications in organic synthesis. Its structural properties make it a valuable intermediate in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. The presence of both electron-donating and electron-withdrawing groups enhances its utility in electrophilic and nucleophilic reactions. The compound exhibits moderate stability under standard conditions, facilitating handling and storage. Its well-defined chemical properties allow for precise functionalization, making it a versatile building block in synthetic chemistry.
1-(4-Hydroxy-3-methoxy-2-nitrophenyl)ethanone structure
1260785-45-2 structure
Product Name:1-(4-Hydroxy-3-methoxy-2-nitrophenyl)ethanone
CAS No:1260785-45-2
MF:C9H9NO5
MW:211.171462774277
CID:824597
PubChem ID:60145949
Update Time:2025-06-13

1-(4-Hydroxy-3-methoxy-2-nitrophenyl)ethanone Chemical and Physical Properties

Names and Identifiers

    • 1-(4-Hydroxy-3-methoxy-2-nitrophenyl)ethanone
    • 1260785-45-2
    • DB-023182
    • BS-50580
    • SY287789
    • DTXSID20733707
    • CS-0130055
    • E77892
    • 4 inverted exclamation mark -Hydroxy-3 inverted exclamation mark -methoxy-2 inverted exclamation mark -nitroacetophenone
    • MFCD11109893
    • 1-(4-Hydroxy-3-methoxy-2-nitrophenyl)ethan-1-one
    • Ethanone, 1-(4-hydroxy-3-methoxy-2-nitrophenyl)-
    • Inchi: 1S/C9H9NO5/c1-5(11)6-3-4-7(12)9(15-2)8(6)10(13)14/h3-4,12H,1-2H3
    • InChI Key: ZOMXLWJRXFETOW-UHFFFAOYSA-N
    • SMILES: O(C)C1=C(C=CC(C(C)=O)=C1[N+](=O)[O-])O

Computed Properties

  • Exact Mass: 211.04807239g/mol
  • Monoisotopic Mass: 211.04807239g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 3
  • Complexity: 262
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.1
  • Topological Polar Surface Area: 92.4?2

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Additional information on 1-(4-Hydroxy-3-methoxy-2-nitrophenyl)ethanone

Introduction to 1-(4-Hydroxy-3-methoxy-2-nitrophenyl)ethanone (CAS No. 1260785-45-2) and Its Emerging Applications in Chemical Biology

The compound 1-(4-Hydroxy-3-methoxy-2-nitrophenyl)ethanone, identified by the CAS number 1260785-45-2, represents a structurally intriguing molecule with significant potential in the field of chemical biology. This review delves into the compound's chemical characteristics, its pharmacological relevance, and its role in contemporary research, emphasizing recent advancements and future prospects.

The molecular framework of 1-(4-Hydroxy-3-methoxy-2-nitrophenyl)ethanone consists of a benzene ring substituted with hydroxyl, methoxy, and nitro groups, linked to an acetyl moiety. This arrangement endows the compound with unique electronic and steric properties, making it a valuable scaffold for drug discovery. The presence of both electron-donating (hydroxyl and methoxy) and electron-withdrawing (nitro) groups creates a balance that enhances its reactivity and biological activity.

In recent years, there has been growing interest in nitroaromatic compounds due to their diverse biological effects. The nitro group in 1-(4-Hydroxy-3-methoxy-2-nitrophenyl)ethanone has been particularly studied for its potential in modulating inflammatory pathways and oxidative stress. Emerging research suggests that this compound may exhibit anti-inflammatory properties by inhibiting key enzymes such as lipoxygenase and cyclooxygenase. These findings align with broader efforts to develop novel therapeutics targeting chronic inflammatory diseases.

Beyond its anti-inflammatory potential, 1-(4-Hydroxy-3-methoxy-2-nitrophenyl)ethanone has shown promise in cancer research. Studies have demonstrated that the compound can induce apoptosis in certain cancer cell lines by disrupting mitochondrial function. The hydroxyl and methoxy groups contribute to its ability to interact with biological targets, enhancing its cytotoxic effects. Furthermore, the nitro group facilitates redox cycling, which can lead to the generation of reactive oxygen species (ROS) that are toxic to cancer cells but less so to healthy tissues.

The synthesis of 1-(4-Hydroxy-3-methoxy-2-nitrophenyl)ethanone is another area of active investigation. Researchers have developed efficient synthetic routes that minimize side reactions and improve yield. These advancements are crucial for scaling up production for both research and clinical applications. The synthesis typically involves nitration of a pre-functionalized benzene derivative followed by condensation with acetyl chloride or acetic anhydride. Optimizing these steps not only enhances efficiency but also ensures the purity of the final product.

From a pharmacokinetic perspective, 1-(4-Hydroxy-3-methoxy-2-nitrophenyl)ethanone exhibits moderate solubility in both water and organic solvents, which is advantageous for formulating it into various delivery systems. Its bioavailability has been assessed in preclinical studies, revealing that it can be effectively absorbed after oral administration. This makes it a suitable candidate for further development into an oral therapeutic agent.

The role of computational chemistry in studying 1-(4-Hydroxy-3-methoxy-2-nitrophenyl)ethanone cannot be overstated. Molecular modeling techniques have been employed to predict its binding interactions with biological targets such as enzymes and receptors. These simulations provide insights into how the compound exerts its effects at the molecular level and help guide the design of more potent derivatives.

In conclusion, 1-(4-Hydroxy-3-methoxy-2-nitrophenyl)ethanone (CAS No. 1260785-45-2) is a multifaceted compound with significant implications in chemical biology and drug discovery. Its unique structural features enable it to interact with various biological pathways, making it a promising candidate for treating inflammatory diseases and cancer. Continued research into its synthesis, pharmacology, and computational properties will further elucidate its potential applications.

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