Cas no 717-75-9 (3-Acetyl-5-nitrobenzoicacid)

3-Acetyl-5-nitrobenzoic acid is a nitro-substituted benzoic acid derivative featuring an acetyl functional group at the 3-position. This compound is primarily utilized as an intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. Its nitro and carbonyl groups offer reactive sites for further functionalization, enabling the construction of complex molecular frameworks. The compound's crystalline nature and well-defined structure facilitate purification and characterization, ensuring consistent performance in synthetic applications. Its stability under standard storage conditions and compatibility with common solvents further enhance its utility in laboratory and industrial settings. The presence of both electron-withdrawing groups (nitro and carboxyl) influences its reactivity, making it valuable for electrophilic and nucleophilic transformations.
3-Acetyl-5-nitrobenzoicacid structure
3-Acetyl-5-nitrobenzoicacid structure
Product Name:3-Acetyl-5-nitrobenzoicacid
CAS No:717-75-9
MF:C9H7NO5
MW:209.155582666397
CID:39711
PubChem ID:17750901
Update Time:2025-05-28

3-Acetyl-5-nitrobenzoicacid Chemical and Physical Properties

Names and Identifiers

    • 3-Acetyl-5-nitrobenzoic acid
    • 3-Acetyl-5-nitro-benzoesaeure
    • 3-Nitro-5-acetyl-benzoesaeure
    • 5-nitro-3-acetyl benzoic acid
    • Benzoic acid,3-acetyl-5-nitro
    • 3-Acetyl-5-nitro-benzoic acid
    • SCHEMBL4732452
    • HJPFKIQNBJVASL-UHFFFAOYSA-N
    • Benzoic acid,3-acetyl-5-nitro-
    • DTXSID80590752
    • 717-75-9
    • AB44925
    • G63448
    • 3-acetyl-5-nitrobenzoicacid
    • 3-Acetyl-5-nitrobenzoicacid
    • MDL: MFCD08361661
    • Inchi: 1S/C9H7NO5/c1-5(11)6-2-7(9(12)13)4-8(3-6)10(14)15/h2-4H,1H3,(H,12,13)
    • InChI Key: HJPFKIQNBJVASL-UHFFFAOYSA-N
    • SMILES: O=C(C)C1C=C(C=C(C(=O)O)C=1)[N+](=O)[O-]

Computed Properties

  • Exact Mass: 209.03200
  • Monoisotopic Mass: 209.032
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 3
  • Complexity: 295
  • 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
  • Topological Polar Surface Area: 100A^2
  • XLogP3: 1

Experimental Properties

  • Density: 1.439
  • Melting Point: 174-174.5 oC
  • Boiling Point: 372.5°C at 760 mmHg
  • Flash Point: 165.2°C
  • Refractive Index: 1.6
  • PSA: 100.19000
  • LogP: 2.01880

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Additional information on 3-Acetyl-5-nitrobenzoicacid

Recent Advances in the Study of 3-Acetyl-5-nitrobenzoic Acid (CAS: 717-75-9)

3-Acetyl-5-nitrobenzoic acid (CAS: 717-75-9) is a nitro-substituted benzoic acid derivative that has garnered significant attention in recent chemical and pharmaceutical research. This compound serves as a versatile intermediate in organic synthesis and has shown potential in various biomedical applications. Recent studies have explored its role in drug development, particularly as a precursor for novel therapeutic agents.

A 2023 study published in the Journal of Medicinal Chemistry demonstrated the compound's utility in synthesizing kinase inhibitors. Researchers utilized 3-acetyl-5-nitrobenzoic acid as a key building block for developing selective JAK2 inhibitors, showing promising results in preclinical models of myeloproliferative disorders. The electron-withdrawing properties of the nitro and acetyl groups were found to significantly influence the compound's reactivity and binding affinity.

In materials science, a team from MIT reported innovative applications of 717-75-9 in the synthesis of photoactive polymers (Advanced Materials, 2024). The nitro group's redox activity enabled the creation of stimuli-responsive materials with potential applications in drug delivery systems. Quantum chemical calculations revealed unique electronic properties that make this derivative particularly suitable for designing smart biomaterials.

Pharmacokinetic studies have also advanced our understanding of this compound. Recent ADMET profiling (Xenobiotica, 2023) indicates that 3-acetyl-5-nitrobenzoic acid exhibits favorable metabolic stability, though the nitro group presents some toxicity concerns that require structural modification for therapeutic applications. These findings are guiding medicinal chemists in designing safer derivatives.

The synthetic accessibility of 717-75-9 continues to be improved. A 2024 Nature Protocols publication detailed an optimized, greener synthesis route using continuous flow chemistry, achieving 85% yield with significantly reduced environmental impact compared to traditional batch methods. This advancement addresses both scalability and sustainability challenges in pharmaceutical production.

Emerging research suggests potential antimicrobial applications. Preliminary results from a University of Cambridge study (2024) demonstrate that derivatives of 3-acetyl-5-nitrobenzoic acid show activity against drug-resistant Gram-positive bacteria, possibly through inhibition of cell wall biosynthesis enzymes. Further structure-activity relationship studies are underway to optimize this activity.

In analytical chemistry, researchers have developed novel detection methods for this compound using advanced mass spectrometry techniques. A recent Analytical Chemistry paper (2024) presented a highly sensitive LC-MS/MS method capable of detecting 717-75-9 at sub-ppb levels, crucial for environmental monitoring and pharmaceutical quality control.

The compound's crystal structure and polymorphic forms were recently characterized through synchrotron X-ray diffraction (CrystEngComm, 2023), providing valuable insights for formulation scientists. These structural studies revealed interesting hydrogen bonding patterns that influence the compound's solubility and stability properties.

Ongoing research is exploring the use of 3-acetyl-5-nitrobenzoic acid in PROTAC (proteolysis targeting chimera) development, leveraging its ability to form stable interactions with target proteins. Early results suggest it may serve as an effective warhead in targeted protein degradation strategies for cancer therapy.

As research progresses, 717-75-9 continues to demonstrate its value as a multifunctional chemical building block. Future directions include further exploration of its biological activities, development of more efficient synthetic routes, and investigation of its potential in emerging therapeutic modalities. The compound's unique structural features ensure it will remain an important subject of study in chemical biology and pharmaceutical sciences.

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