Cas no 136507-14-7 (2-Methoxy-4-nitrobenzyl alcohol)

2-Methoxy-4-nitrobenzyl alcohol is a nitroaromatic compound with the molecular formula C?H?NO?. It features a benzyl alcohol core substituted with a methoxy group at the 2-position and a nitro group at the 4-position, imparting distinct reactivity for synthetic applications. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. Its nitro and hydroxyl functional groups enable selective transformations, such as reductions or etherifications, making it valuable for constructing complex molecular architectures. The methoxy group enhances solubility in organic solvents, facilitating purification and handling. Suitable for controlled reactions, it offers a balance of stability and reactivity for targeted synthetic pathways.
2-Methoxy-4-nitrobenzyl alcohol structure
136507-14-7 structure
Product Name:2-Methoxy-4-nitrobenzyl alcohol
CAS No:136507-14-7
MF:C8H9NO4
MW:183.161362409592
MDL:MFCD08277262
CID:901224
PubChem ID:10487701
Update Time:2025-06-12

2-Methoxy-4-nitrobenzyl alcohol Chemical and Physical Properties

Names and Identifiers

    • (2-Methoxy-4-nitrophenyl)methanol
    • 2-Methoxy-4-nitrobenzyl alcohol
    • (2-methoxy-4-nitrophenyl)methan-1-ol
    • SCHEMBL13981885
    • D83036
    • IWXYLEKOKGKRTN-UHFFFAOYSA-N
    • XH0846
    • DTXSID30440692
    • CS-0150547
    • AKOS006285009
    • SY346047
    • 136507-14-7
    • SCHEMBL357288
    • MFCD08277262
    • AB44873
    • EN300-191377
    • Benzenemethanol, 2-methoxy-4-nitro-
    • BS-15304
    • MDL: MFCD08277262
    • Inchi: 1S/C8H9NO4/c1-13-8-4-7(9(11)12)3-2-6(8)5-10/h2-4,10H,5H2,1H3
    • InChI Key: IWXYLEKOKGKRTN-UHFFFAOYSA-N
    • SMILES: O(C)C1C=C(C=CC=1CO)[N+](=O)[O-]

Computed Properties

  • Exact Mass: 183.05300
  • Monoisotopic Mass: 183.05315777g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 3
  • Complexity: 180
  • 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: 0.8
  • Topological Polar Surface Area: 75.3?2

Experimental Properties

  • Density: 1.317
  • Boiling Point: 357.4°C at 760 mmHg
  • Flash Point: 169.95°C
  • Refractive Index: 1.574
  • PSA: 75.28000
  • LogP: 1.61890

2-Methoxy-4-nitrobenzyl alcohol Pricemore >>

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2-Methoxy-4-nitrobenzyl alcohol Production Method

Additional information on 2-Methoxy-4-nitrobenzyl alcohol

Research Briefing on 2-Methoxy-4-nitrobenzyl alcohol (CAS: 136507-14-7) in Chemical Biology and Pharmaceutical Applications

2-Methoxy-4-nitrobenzyl alcohol (CAS: 136507-14-7) is a specialized chemical compound that has garnered significant attention in the field of chemical biology and pharmaceutical research. This compound, characterized by its nitrobenzyl moiety and methoxy functional group, serves as a versatile intermediate in the synthesis of various bioactive molecules. Recent studies have explored its potential applications in photolabile protecting groups, prodrug design, and as a scaffold for developing novel therapeutic agents. This briefing synthesizes the latest findings and highlights the compound's role in advancing research and development efforts.

One of the primary areas of interest for 2-Methoxy-4-nitrobenzyl alcohol is its utility in photolabile protecting groups. Researchers have leveraged its ability to undergo photochemical cleavage upon exposure to specific wavelengths of light, making it invaluable in controlled release systems. A 2023 study published in the Journal of Photochemistry and Photobiology demonstrated its efficacy in protecting carboxylic acids and amines, with subsequent release achieved under mild UV irradiation. This property is particularly advantageous in targeted drug delivery systems, where spatial and temporal control over drug release is critical.

In addition to its photochemical applications, 2-Methoxy-4-nitrobenzyl alcohol has been investigated for its role in prodrug development. A recent publication in Bioorganic & Medicinal Chemistry Letters highlighted its use as a masking group for phenolic hydroxyl functionalities in prodrugs. The study reported enhanced stability and bioavailability of the prodrugs in physiological conditions, with the nitrobenzyl alcohol moiety facilitating selective activation in target tissues. This approach holds promise for improving the pharmacokinetic profiles of existing therapeutics, particularly in oncology and anti-inflammatory treatments.

Furthermore, the compound's structural features have made it a valuable building block in medicinal chemistry. Research published in ACS Medicinal Chemistry Letters in early 2024 detailed its incorporation into novel small-molecule inhibitors targeting protein-protein interactions. The nitro and methoxy groups were found to contribute to favorable binding affinities and selectivity, underscoring the compound's potential in drug discovery. Computational modeling and crystallographic studies provided insights into the molecular interactions, paving the way for rational design of next-generation therapeutics.

The synthesis and scalability of 2-Methoxy-4-nitrobenzyl alcohol have also been subjects of recent optimization efforts. A 2023 study in Organic Process Research & Development presented a streamlined synthetic route with improved yields and reduced environmental impact. The use of green chemistry principles, such as catalytic hydrogenation and solvent recycling, was emphasized, aligning with the pharmaceutical industry's growing focus on sustainability. These advancements are expected to facilitate broader adoption of the compound in both academic and industrial settings.

Looking ahead, researchers are exploring the potential of 2-Methoxy-4-nitrobenzyl alcohol in emerging areas such as bioorthogonal chemistry and chemical biology tools. Preliminary results from a multinational collaboration suggest its applicability in designing activity-based probes for enzyme profiling, with findings anticipated to be published later this year. As the compound continues to demonstrate versatility across multiple domains, it remains a focal point for innovation in chemical biology and pharmaceutical sciences.

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