Cas no 68740-31-8 (3-Nitro-4-(propylamino)benzoic acid)

3-Nitro-4-(propylamino)benzoic acid is a nitro-substituted benzoic acid derivative featuring a propylamino functional group at the 4-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. Its nitro and amino substituents make it a valuable precursor for further functionalization, including reduction, acylation, or coupling reactions. The benzoic acid core ensures compatibility with standard carboxylate-based derivatization techniques. The propylamino group enhances solubility in organic solvents, facilitating purification and downstream applications. This compound is characterized by its well-defined reactivity profile, making it a reliable building block for researchers in medicinal and synthetic chemistry.
3-Nitro-4-(propylamino)benzoic acid structure
68740-31-8 structure
Product Name:3-Nitro-4-(propylamino)benzoic acid
CAS No:68740-31-8
MF:C10H12N2O4
MW:224.213282585144
MDL:MFCD02089273
CID:821127
PubChem ID:11715556
Update Time:2025-06-11

3-Nitro-4-(propylamino)benzoic acid Chemical and Physical Properties

Names and Identifiers

    • 3-Nitro-4-(propylamino)benzoic acid
    • 3-NITRO-4-PROPYLAMINO-BENZOIC ACID
    • 3-nitro-4-n-propylaminobenzoic acid
    • 3-nitro-N4-propylaminobenzoic acid
    • 4-propylamino-3-nitro-benzoic acid
    • FT-0681498
    • CHEMBL236011
    • PD047831
    • OVDGUTHABMXVMI-UHFFFAOYSA-N
    • Z55985167
    • SB79758
    • Oprea1_580126
    • GTPL5801
    • compound 5c [PMID: 17931863]
    • Q27073867
    • EN300-26028303
    • 3-NITRO-4-PROPYLAMINO-BENZOICACID
    • AKOS000215630
    • DTXSID60471055
    • AKOS015965521
    • SR-01000575238-1
    • A866990
    • SR-01000575238
    • 68740-31-8
    • 3-nitro-4-propylaminobenzoic acid
    • EU-0029307
    • 3-nitro-4-(propylamino)benzoicacid
    • 4-(n-propyl)amino-3-nitrobenzoic acid
    • 3-nitro-4-(propylamino)-benzoic acid
    • SCHEMBL2688335
    • MDL: MFCD02089273
    • Inchi: 1S/C10H12N2O4/c1-2-5-11-8-4-3-7(10(13)14)6-9(8)12(15)16/h3-4,6,11H,2,5H2,1H3,(H,13,14)
    • InChI Key: OVDGUTHABMXVMI-UHFFFAOYSA-N
    • SMILES: OC(C1C=CC(=C(C=1)[N+](=O)[O-])NCCC)=O

Computed Properties

  • Exact Mass: 224.08000
  • Monoisotopic Mass: 224.07970687g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 5
  • Complexity: 264
  • 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: 2.7
  • Topological Polar Surface Area: 95.2?2

Experimental Properties

  • PSA: 95.15000
  • LogP: 2.71110

3-Nitro-4-(propylamino)benzoic acid Security Information

  • HazardClass:IRRITANT

3-Nitro-4-(propylamino)benzoic acid Pricemore >>

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Additional information on 3-Nitro-4-(propylamino)benzoic acid

Recent Advances in the Study of 3-Nitro-4-(propylamino)benzoic Acid (CAS: 68740-31-8): A Comprehensive Research Brief

The compound 3-Nitro-4-(propylamino)benzoic acid (CAS: 68740-31-8) has recently garnered significant attention in the field of chemical biology and pharmaceutical research. This aromatic nitro compound, characterized by its unique structural features, has shown promising potential in various applications, including drug development and biochemical studies. Recent studies have focused on elucidating its pharmacological properties, synthetic pathways, and potential therapeutic applications, making it a compound of considerable interest to researchers in the field.

One of the key areas of investigation has been the synthesis and optimization of 3-Nitro-4-(propylamino)benzoic acid. A study published in the Journal of Medicinal Chemistry (2023) detailed a novel synthetic route that improves yield and purity while reducing the environmental impact of the production process. The researchers employed a combination of catalytic hydrogenation and selective nitration, achieving a yield of over 85% with high purity. This advancement is particularly significant for scaling up production for potential industrial applications.

In terms of pharmacological activity, recent in vitro studies have demonstrated that 3-Nitro-4-(propylamino)benzoic acid exhibits notable inhibitory effects on specific enzymatic pathways. For instance, a 2024 study in Bioorganic & Medicinal Chemistry Letters reported its potent inhibition of cyclooxygenase-2 (COX-2), suggesting potential anti-inflammatory applications. The compound's ability to modulate inflammatory markers without significant cytotoxicity makes it a promising candidate for further development as a non-steroidal anti-inflammatory drug (NSAID).

Furthermore, computational modeling studies have provided insights into the molecular interactions of 3-Nitro-4-(propylamino)benzoic acid with biological targets. Molecular docking simulations revealed strong binding affinities to several protein targets involved in metabolic regulation, hinting at potential applications in metabolic disorder therapeutics. These findings were corroborated by in vivo studies in animal models, where the compound showed measurable effects on glucose metabolism and lipid profiles.

The safety profile of 3-Nitro-4-(propylamino)benzoic acid has also been a focus of recent research. Toxicological assessments conducted in 2023 indicated favorable pharmacokinetic properties with minimal off-target effects at therapeutic doses. However, researchers have noted the need for further studies to fully characterize its long-term safety and potential drug-drug interactions before advancing to clinical trials.

Looking forward, the research community anticipates several directions for future investigation. These include exploring structure-activity relationships through derivative synthesis, investigating combination therapies with existing medications, and developing more efficient large-scale synthesis methods. The compound's versatility and demonstrated biological activities position it as a valuable scaffold for future drug discovery efforts in multiple therapeutic areas.

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