Cas no 53055-04-2 ((3-Methoxy-2-nitrophenyl)methanol)

(3-Methoxy-2-nitrophenyl)methanol is a versatile aromatic compound featuring both methoxy and nitro substituents on a benzyl alcohol scaffold. Its distinct structure makes it a valuable intermediate in organic synthesis, particularly for the preparation of pharmaceuticals, agrochemicals, and specialty chemicals. The presence of the electron-donating methoxy group and electron-withdrawing nitro group allows for selective functionalization, enabling applications in cross-coupling reactions and heterocycle formation. The benzylic alcohol moiety further enhances reactivity, facilitating derivatization into esters, ethers, or aldehydes. This compound exhibits high purity and stability under standard storage conditions, ensuring reliable performance in synthetic workflows. Its well-defined reactivity profile makes it a preferred choice for researchers developing novel molecular architectures.
(3-Methoxy-2-nitrophenyl)methanol structure
53055-04-2 structure
Product Name:(3-Methoxy-2-nitrophenyl)methanol
CAS No:53055-04-2
MF:C8H9NO4
MW:183.161362409592
CID:1028412
PubChem ID:10375096
Update Time:2025-05-20

(3-Methoxy-2-nitrophenyl)methanol Chemical and Physical Properties

Names and Identifiers

    • (3-Methoxy-2-nitrophenyl)methanol
    • (2-NITRO-3-METHOXY-PHENYL)-METHANOL
    • 3-methoxy-2-nitroBenzenemethanol
    • (2-Nitro-3-methoxyphenyl)-methanol
    • 3-methoxy-2-nitro-benzyl alcohol
    • 3-Methoxy-2-nitrobenzylalkohol
    • 3-Methoxy-2-nitro-benzylalkohol
    • AG-L-59364
    • AK137777
    • CTK4J6950
    • QC-8568
    • RP24391
    • DTXSID20438861
    • 2-Nitro-3-methoxybenzyl alcohol
    • 3-Methoxy-2-nitrobenzyl alcohol
    • J-500886
    • (3-methoxy-2-nitro-phenyl)methanol
    • CS-0096356
    • DA-23463
    • EN300-1848447
    • TD8204
    • SCHEMBL16154026
    • (2-Nitro-3-methoxyphenyl)methanol
    • MFCD06202768
    • SY317023
    • 53055-04-2
    • CS-16374
    • AKOS006295226
    • Inchi: 1S/C8H9NO4/c1-13-7-4-2-3-6(5-10)8(7)9(11)12/h2-4,10H,5H2,1H3
    • InChI Key: YYIIAPQEOXNDLW-UHFFFAOYSA-N
    • SMILES: O(C)C1=CC=CC(CO)=C1[N+](=O)[O-]

Computed Properties

  • Exact Mass: 183.05317
  • 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

  • PSA: 72.6

(3-Methoxy-2-nitrophenyl)methanol Pricemore >>

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Additional information on (3-Methoxy-2-nitrophenyl)methanol

Recent Advances in the Study of (3-Methoxy-2-nitrophenyl)methanol (CAS: 53055-04-2) and Its Applications in Chemical Biology and Pharmaceutical Research

The compound (3-Methoxy-2-nitrophenyl)methanol (CAS: 53055-04-2) has recently garnered significant attention in the field of chemical biology and pharmaceutical research. This aromatic alcohol derivative, characterized by its methoxy and nitro functional groups, has demonstrated potential as a versatile intermediate in the synthesis of bioactive molecules. Recent studies have explored its utility in drug discovery, particularly in the development of novel therapeutic agents targeting inflammatory and oncological pathways. The compound's unique structural features enable its incorporation into more complex pharmacophores, enhancing binding affinity and selectivity.

In a 2023 study published in the Journal of Medicinal Chemistry, researchers investigated the role of (3-Methoxy-2-nitrophenyl)methanol as a precursor in the synthesis of small-molecule inhibitors for protein kinases. The study highlighted its efficacy in forming stable covalent bonds with cysteine residues in the ATP-binding pocket of kinases, thereby inhibiting aberrant signaling pathways implicated in cancer progression. The researchers employed density functional theory (DFT) calculations to optimize the compound's reactivity, followed by in vitro assays to validate its inhibitory effects on tumor cell lines.

Another notable application of (3-Methoxy-2-nitrophenyl)methanol was reported in a recent ACS Chemical Biology article, where it was utilized as a key building block for the development of fluorescent probes. These probes were designed to detect reactive oxygen species (ROS) in live cells, offering insights into oxidative stress mechanisms associated with neurodegenerative diseases. The nitro group in the compound facilitated the probe's redox-sensitive properties, while the methanol moiety allowed for further functionalization with fluorophores. The study demonstrated high specificity and sensitivity in detecting ROS in neuronal models, paving the way for diagnostic applications.

Beyond its role in drug discovery and diagnostics, (3-Methoxy-2-nitrophenyl)methanol has also been explored in materials science. A 2024 Nature Communications paper detailed its incorporation into polymer matrices to create stimuli-responsive materials. The nitro group's photolabile nature enabled the development of light-triggered drug delivery systems, where the compound acted as a photocleavable linker. This innovation holds promise for targeted therapies, minimizing off-target effects and improving therapeutic outcomes.

Despite these advancements, challenges remain in the large-scale synthesis and purification of (3-Methoxy-2-nitrophenyl)methanol. A recent Organic Process Research & Development study addressed these issues by optimizing catalytic hydrogenation conditions to improve yield and reduce byproduct formation. The authors proposed a green chemistry approach using palladium-on-carbon catalysts under mild conditions, achieving a 90% yield with high purity. This methodological improvement is expected to facilitate broader adoption of the compound in industrial applications.

In conclusion, (3-Methoxy-2-nitrophenyl)methanol (CAS: 53055-04-2) represents a multifaceted tool in chemical biology and pharmaceutical research. Its applications span drug development, diagnostic probes, and advanced materials, underscoring its versatility. Future research should focus on expanding its utility in targeted therapies and exploring its potential in other disease models. The compound's unique properties and recent methodological advances position it as a valuable asset in the pursuit of innovative therapeutic solutions.

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