Cas no 133486-62-1 (1-(bromomethyl)-3-methoxy-2-nitrobenzene)

1-(Bromomethyl)-3-methoxy-2-nitrobenzene is a brominated aromatic compound featuring a methoxy and nitro substituent on the benzene ring. Its reactive bromomethyl group makes it a valuable intermediate in organic synthesis, particularly for nucleophilic substitution reactions. The presence of electron-withdrawing nitro and electron-donating methoxy groups enhances its utility in regioselective transformations. This compound is commonly employed in pharmaceutical and agrochemical research for constructing complex molecular frameworks. Its stability under standard conditions and well-defined reactivity profile contribute to its reliability in multi-step synthetic routes. The compound is typically handled under controlled conditions due to the lachrymatory nature of bromomethyl derivatives.
1-(bromomethyl)-3-methoxy-2-nitrobenzene structure
133486-62-1 structure
Product Name:1-(bromomethyl)-3-methoxy-2-nitrobenzene
CAS No:133486-62-1
MF:C8H8BrNO3
MW:246.05802154541
CID:1232967
PubChem ID:10332134
Update Time:2025-10-29

1-(bromomethyl)-3-methoxy-2-nitrobenzene Chemical and Physical Properties

Names and Identifiers

    • 1-(bromomethyl)-3-methoxy-2-nitrobenzene
    • SCHEMBL6967217
    • EN300-1895102
    • AKOS014097314
    • AB50501
    • F20199
    • 133486-62-1
    • A888082
    • DTXSID20438265
    • DA-12058
    • MDL: MFCD09264063
    • Inchi: 1S/C8H8BrNO3/c1-13-7-4-2-3-6(5-9)8(7)10(11)12/h2-4H,5H2,1H3
    • InChI Key: OGGQVUNUXHDQNZ-UHFFFAOYSA-N
    • SMILES: BrCC1C=CC=C(C=1[N+](=O)[O-])OC

Computed Properties

  • Exact Mass: 244.96876g/mol
  • Monoisotopic Mass: 244.96876g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 3
  • Complexity: 183
  • 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: 2.3
  • Topological Polar Surface Area: 55?2

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1-(bromomethyl)-3-methoxy-2-nitrobenzene Related Literature

Additional information on 1-(bromomethyl)-3-methoxy-2-nitrobenzene

Exploring the Synthesis and Applications of 1-(Bromomethyl)-3-Methoxy-2-Nitrobenzene (CAS No. 133486-62-1)

The compound 1-(Bromomethyl)-3-methoxy-2-nitrobenzene, identified by CAS No. 133486-62-1, represents a versatile aromatic intermediate with distinct functional groups that enable its application across diverse research domains. Its structure features a nitro group at the 2-position, a methoxy substituent at the 3-position, and a bromomethyl moiety at the 1-position, creating a platform for chemical modifications. Recent advancements in synthetic methodologies have enhanced its utility in drug discovery, materials science, and analytical chemistry.

The bromomethyl group plays a critical role in enabling nucleophilic substitution reactions, which are pivotal for synthesizing bioactive molecules. For instance, studies published in Journal of Medicinal Chemistry (2023) demonstrated its use as an intermediate in developing nitro-containing anticancer agents. Researchers leveraged the bromomethyl functionality to attach targeting ligands, improving drug specificity toward cancer cells while maintaining the inherent cytotoxicity of nitroaromatic compounds. This approach highlights how structural flexibility derived from the compound’s substituents drives innovation in targeted therapeutics.

In materials research, the compound’s electronic properties have been exploited for designing novel optoelectronic materials. A 2024 study in Nano Letters revealed that polymerized derivatives exhibit tunable fluorescence emission due to synergistic effects between the nitro and methoxy groups. By modulating reaction conditions during synthesis—such as varying solvent polarity or catalyst loading—researchers achieved precise control over photophysical characteristics, making these materials candidates for next-generation sensors and bioimaging probes.

Synthetic strategies for accessing this compound have evolved to prioritize sustainability. Traditional methods involving Friedel-Crafts acylation were historically employed but often required hazardous reagents. Recent protocols published in Green Chemistry (2024) introduced microwave-assisted synthesis using environmentally benign catalysts like heterogeneous sulfonic acid-functionalized silica. This approach reduced reaction times by up to 70% while minimizing waste production, aligning with global trends toward greener chemical practices.

In analytical chemistry, derivatization reactions with this compound enable selective detection of biomolecules. A notable application involves conjugation with carbohydrates to create fluorescent markers for glycoprotein analysis. Work from the University of Cambridge (Nature Communications, 2024) showcased how its unique reactivity allowed site-specific labeling without perturbing protein structures—a breakthrough for studying glycosylation pathways in live cells.

Ongoing research focuses on optimizing its use as an intermediate in multistep organic syntheses. Computational modeling studies predict that substituting the methoxy group with electron-withdrawing groups could enhance metabolic stability in pharmaceutical candidates. Meanwhile, crystal engineering efforts aim to exploit its molecular geometry for creating supramolecular assemblies with programmable self-assembly behaviors.

The integration of machine learning into synthetic planning has further accelerated discoveries involving this compound. AI-driven platforms like IBM’s RXN for Chemistry identified novel reaction pathways that utilize its bromomethyl group as a handle for constructing polycyclic scaffolds—a strategy now adopted by several pharmaceutical companies to streamline lead optimization processes.

In conclusion, CAS No. 133486-62-1 continues to serve as a foundational building block across disciplines due to its chemically tunable architecture and well-characterized reactivity profile. As interdisciplinary collaborations between chemists and biologists expand—particularly in areas like precision medicine and smart materials—the demand for advanced derivatives will drive further innovations rooted in this compound’s fundamental properties.

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