Cas no 59338-90-8 (4-Amino-2-methoxy-5-nitro-benzoic Acid)

4-Amino-2-methoxy-5-nitro-benzoic Acid is a versatile organic compound featuring a nitro group, amino group, and methoxy group. Its structural diversity enables applications in organic synthesis, serving as a precursor for the preparation of various pharmaceuticals and dyes. This compound exhibits excellent solubility in organic solvents, facilitating synthetic procedures. Its distinct functional groups contribute to its reactivity, making it a valuable building block in chemical reactions.
4-Amino-2-methoxy-5-nitro-benzoic Acid structure
59338-90-8 structure
Product Name:4-Amino-2-methoxy-5-nitro-benzoic Acid
CAS No:59338-90-8
MF:C8H8N2O5
MW:212.15952205658
MDL:MFCD09908199
CID:375893
PubChem ID:101016
Update Time:2025-07-14

4-Amino-2-methoxy-5-nitro-benzoic Acid Chemical and Physical Properties

Names and Identifiers

    • Benzoic acid,4-amino-2-methoxy-5-nitro-
    • 4-Amino-5-nitro-o-anisic acid
    • 4-AMINO-2-METHOXY-5-NITRO-BENZOIC ACID
    • AMY18304
    • EINECS 261-706-4
    • 2-methoxy-4-amino-5-nitro benzoic acid
    • Z1869801767
    • CS-0233447
    • 59338-90-8
    • EN300-133638
    • 4-amino-2-methoxy-5-nitrobenzoic acid
    • AKOS015889990
    • AOANPIGDKLHHIC-UHFFFAOYSA-N
    • A832274
    • SB79287
    • SCHEMBL1725804
    • 2-methoxy-4-amino-5-nitrobenzoic acid
    • 4-amino-2-methoxy-5-nitrobenzoicacid
    • G10247
    • NS00056849
    • DTXSID30974760
    • DB-229048
    • 4-Amino-2-methoxy-5-nitrobenzoic acid methyl ester
    • 4-Amino-2-methoxy-5-nitro-benzoic Acid
    • MDL: MFCD09908199
    • Inchi: 1S/C8H8N2O5/c1-15-7-3-5(9)6(10(13)14)2-4(7)8(11)12/h2-3H,9H2,1H3,(H,11,12)
    • InChI Key: AOANPIGDKLHHIC-UHFFFAOYSA-N
    • SMILES: O(C)C1C=C(C(=CC=1C(=O)O)[N+](=O)[O-])N

Computed Properties

  • Exact Mass: 212.04334
  • Monoisotopic Mass: 212.043
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 15
  • Rotatable Bond Count: 3
  • 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: 1.6
  • Topological Polar Surface Area: 118?2

Experimental Properties

  • PSA: 115.69

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Additional information on 4-Amino-2-methoxy-5-nitro-benzoic Acid

Introduction to 4-Amino-2-methoxy-5-nitro-benzoic Acid (CAS No. 59338-90-8)

4-Amino-2-methoxy-5-nitro-benzoic Acid, identified by its Chemical Abstracts Service (CAS) number 59338-90-8, is a significant compound in the realm of chemical and pharmaceutical research. This heterocyclic aromatic acid features a nitro and amino substituent on a benzoic acid backbone, with an additional methoxy group at the 2-position. Its unique structural configuration makes it a valuable intermediate in synthesizing various bioactive molecules, particularly in medicinal chemistry and drug development.

The compound's molecular formula, C?H?NO?, underscores its complexity and potential reactivity. The presence of both electron-withdrawing (nitro) and electron-donating (amino and methoxy) groups imparts distinct chemical properties, making it a versatile building block for designing novel therapeutic agents. In recent years, the interest in 4-Amino-2-methoxy-5-nitro-benzoic Acid has surged due to its applications in developing targeted therapies for diverse diseases.

One of the most compelling aspects of 4-Amino-2-methoxy-5-nitro-benzoic Acid is its role in the synthesis of inhibitors targeting specific enzymatic pathways. For instance, researchers have leveraged its structural framework to create potent inhibitors of polyphenol oxidases, which are implicated in oxidative stress-related disorders. The nitro group enhances electrophilicity, facilitating further functionalization, while the amino and methoxy groups provide steric and electronic tuning for optimal binding affinity.

Recent studies have highlighted the compound's utility in designing small-molecule probes for biochemical assays. Its ability to act as a substrate or inhibitor for various enzymes has made it a cornerstone in high-throughput screening (HTS) campaigns. Notably, derivatives of 4-Amino-2-methoxy-5-nitro-benzoic Acid have shown promise in modulating pathways associated with inflammation and neurodegeneration. These findings underscore the compound's potential as a scaffold for developing next-generation therapeutics.

The pharmaceutical industry has also explored 4-Amino-2-methoxy-5-nitro-benzoic Acid as a precursor for synthesizing anti-inflammatory agents. Its structural motif is reminiscent of several known drugs that target cyclooxygenase (COX) enzymes, which play a pivotal role in prostaglandin synthesis. By modifying key functional groups, chemists can fine-tune the pharmacological profile of derived compounds to achieve desired therapeutic effects while minimizing side effects.

In addition to its medicinal applications, 4-Amino-2-methoxy-5-nitro-benzoic Acid finds utility in analytical chemistry and material science. Its distinct spectral properties make it suitable for use as a chromophore in fluorescent probes and sensors. Researchers have employed this compound to develop highly sensitive detection methods for environmental pollutants and biomarkers in clinical diagnostics. The versatility of its structure allows for further derivatization, enabling tailored solutions for specific analytical challenges.

The synthesis of 4-Amino-2-methoxy-5-nitro-benzoic Acid typically involves multi-step organic reactions, starting from commercially available benzoic acid derivatives. Nitration followed by selective methylation and reduction are common strategies employed to introduce the desired functional groups at specific positions on the aromatic ring. Advances in synthetic methodologies have improved the efficiency and scalability of these processes, making CAS No. 59338-90-8 more accessible for research purposes.

The growing body of literature on 4-Amino-2-methoxy-5-nitro-benzoic Acid reflects its importance as a chemical entity with broad applications. From drug discovery to environmental monitoring, this compound continues to inspire innovation across multiple scientific disciplines. As research progresses, new derivatives and applications are likely to emerge, further solidifying its position as a cornerstone molecule in modern chemistry.

In conclusion, 4-Amino-2-methoxy-5-nitro-benzoic Acid (CAS No. 59338-90-8) is a multifaceted compound with significant implications in pharmaceuticals, analytical chemistry, and material science. Its unique structural features enable diverse applications, from developing targeted therapeutics to creating advanced diagnostic tools. The continued exploration of this molecule promises to yield groundbreaking advancements in science and medicine.

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