Cas no 26697-35-8 (4-Benzyloxy-2-nitroaniline)

4-Benzyloxy-2-nitroaniline is a nitro-substituted aniline derivative featuring a benzyloxy functional group at the para position. This compound is primarily utilized as an intermediate in organic synthesis, particularly in the preparation of dyes, pharmaceuticals, and agrochemicals. Its nitro and amino groups offer reactivity for further functionalization, enabling the construction of more complex molecular architectures. The benzyloxy moiety enhances solubility in organic solvents, facilitating its use in various reaction conditions. This compound is valued for its stability under typical storage conditions and its role in facilitating selective transformations in multi-step synthetic routes. Proper handling is advised due to potential sensitivity to light and moisture.
4-Benzyloxy-2-nitroaniline structure
4-Benzyloxy-2-nitroaniline structure
Product Name:4-Benzyloxy-2-nitroaniline
CAS No:26697-35-8
MF:C13H12N2O3
MW:244.245983123779
MDL:MFCD00024263
CID:852242
PubChem ID:261497
Update Time:2025-05-27

4-Benzyloxy-2-nitroaniline Chemical and Physical Properties

Names and Identifiers

    • 4-(Benzyloxy)-2-nitroaniline
    • 4-Benzyloxy-2-nitroaniline
    • 2-nitro-4-phenylmethoxy-aniline
    • 4-(benzyloxy)-2-nitrobenzenamine
    • 2-nitro-4-phenylmethoxyaniline
    • NSC-93775
    • CHEMBL1700660
    • SCHEMBL810368
    • CS-W012739
    • JGVXQZRIRQLMHA-UHFFFAOYSA-N
    • Z991908684
    • DTXSID00294043
    • MFCD00024263
    • STL276071
    • SB80615
    • EN300-155777
    • AKOS016007397
    • 26697-35-8
    • 2-Nitro-4-(benzyloxy)aniline
    • HMS3087G11
    • 2-Nitro-4-(phenylmethoxy)benzenamine; Aniline, 4-(benzyloxy)-2-nitro- (8CI); (4-Benzyloxy-2-nitrophenyl)amine; 2-Nitro-4-(benzyloxy)aniline; 4-(Benzyloxy)-2-nitroaniline; NSC 93775
    • DA-22329
    • 4-Benzyloxy-2-nitro-phenylamine
    • AS-58853
    • J-016519
    • SMR001561121
    • A877162
    • NSC93775
    • 1-amino-4-benzyloxy-2-nitrobenzene
    • MLS002695211
    • MDL: MFCD00024263
    • Inchi: 1S/C13H12N2O3/c14-12-7-6-11(8-13(12)15(16)17)18-9-10-4-2-1-3-5-10/h1-8H,9,14H2
    • InChI Key: JGVXQZRIRQLMHA-UHFFFAOYSA-N
    • SMILES: O(C1=CC=C(C(=C1)[N+](=O)[O-])N)CC1C=CC=CC=1

Computed Properties

  • Exact Mass: 244.08500
  • Monoisotopic Mass: 244.08479225g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 18
  • Rotatable Bond Count: 4
  • Complexity: 274
  • 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: 3.4
  • Topological Polar Surface Area: 81.1?2

Experimental Properties

  • Density: 1.3±0.1 g/cm3
  • Melting Point: 141-143°C
  • Boiling Point: 443.6±30.0 °C at 760 mmHg
  • Flash Point: 222.1±24.6 °C
  • PSA: 81.07000
  • LogP: 3.86040
  • Vapor Pressure: 0.0±1.1 mmHg at 25°C

4-Benzyloxy-2-nitroaniline Security Information

4-Benzyloxy-2-nitroaniline Customs Data

  • HS CODE:2922199090
  • Customs Data:

    China Customs Code:

    2922199090

    Overview:

    2922199090. Other amino alcohols and their ethers,Esters and their salts(Except those containing more than one oxygen-containing group). VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:30.0%

    Declaration elements:

    Product Name, component content, use to, The color of ethanolamine and its salt should be reported, The package of ethanolamine and its salt shall be declared

    Summary:

    2922199090. other amino-alcohols, other than those containing more than one kind of oxygen function, their ethers and esters; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

4-Benzyloxy-2-nitroaniline Pricemore >>

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4-Benzyloxy-2-nitroaniline Production Method

Additional information on 4-Benzyloxy-2-nitroaniline

Recent Advances in the Study of 4-Benzyloxy-2-nitroaniline (CAS: 26697-35-8) and Its Applications in Chemical Biology and Pharmaceutical Research

The compound 4-Benzyloxy-2-nitroaniline (CAS: 26697-35-8) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural properties and potential applications in drug discovery and development. This research brief aims to provide an overview of the latest findings related to this compound, focusing on its synthesis, biological activities, and potential therapeutic uses. Recent studies have highlighted its role as a key intermediate in the synthesis of more complex molecules, as well as its direct biological effects in various experimental models.

One of the most notable advancements in the study of 4-Benzyloxy-2-nitroaniline is its application in the development of novel antimicrobial agents. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that derivatives of this compound exhibit potent activity against a range of Gram-positive and Gram-negative bacteria, including methicillin-resistant Staphylococcus aureus (MRSA). The researchers attributed this activity to the compound's ability to disrupt bacterial cell wall synthesis, a mechanism that differs from currently available antibiotics, suggesting potential for addressing antibiotic resistance.

In addition to its antimicrobial properties, recent investigations have explored the anticancer potential of 4-Benzyloxy-2-nitroaniline derivatives. A team from the University of Cambridge reported in Bioorganic & Medicinal Chemistry Letters that certain structural modifications of this compound resulted in selective cytotoxicity against various cancer cell lines, particularly those associated with breast and colon cancers. The study identified the nitro group as a crucial pharmacophore, with its reduction potential playing a significant role in the compound's mechanism of action.

The synthesis and optimization of 4-Benzyloxy-2-nitroaniline have also seen significant progress. A 2024 paper in Organic Process Research & Development described a novel, scalable synthetic route that improves yield and reduces environmental impact compared to traditional methods. This advancement is particularly important for potential industrial-scale production, addressing one of the key challenges in translating laboratory findings to clinical applications.

From a mechanistic perspective, computational chemistry studies have provided new insights into the molecular interactions of 4-Benzyloxy-2-nitroaniline with biological targets. Molecular docking simulations published in Journal of Chemical Information and Modeling revealed specific binding patterns with various enzymes, supporting the experimental findings of its biological activities. These computational approaches are facilitating the rational design of more potent and selective derivatives.

Despite these promising developments, challenges remain in the clinical translation of 4-Benzyloxy-2-nitroaniline-based therapeutics. Current research is focusing on improving the compound's pharmacokinetic properties, particularly its solubility and metabolic stability. Several research groups are employing prodrug strategies and formulation technologies to address these limitations, with preliminary results showing encouraging improvements in bioavailability.

Looking forward, the versatility of 4-Benzyloxy-2-nitroaniline as a chemical scaffold suggests potential applications beyond antimicrobial and anticancer therapies. Recent patent applications indicate growing interest in its use for developing treatments for neurological disorders and inflammatory conditions. The compound's ability to modulate various biological pathways positions it as a valuable tool for both therapeutic development and fundamental research in chemical biology.

In conclusion, the ongoing research on 4-Benzyloxy-2-nitroaniline (CAS: 26697-35-8) demonstrates its significant potential in pharmaceutical development. The compound serves as both a valuable intermediate in organic synthesis and a promising lead for drug discovery. As research continues to elucidate its mechanisms of action and optimize its pharmacological properties, we anticipate seeing more advanced derivatives entering preclinical and clinical development in the coming years.

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