Cas no 57684-71-6 (3-(Chloromethyl)isoxazole)

3-(Chloromethyl)isoxazole is a versatile heterocyclic compound featuring a reactive chloromethyl group attached to an isoxazole ring. This structure makes it a valuable intermediate in organic synthesis, particularly for the preparation of pharmaceuticals, agrochemicals, and functional materials. The chloromethyl group enables facile nucleophilic substitution reactions, allowing for the introduction of the isoxazole moiety into more complex molecules. Its stability under standard conditions and compatibility with a range of reaction conditions enhance its utility in multi-step syntheses. The compound’s well-defined reactivity profile and high purity make it a reliable choice for researchers seeking to modify or derivatize isoxazole-based scaffolds efficiently.
3-(Chloromethyl)isoxazole structure
3-(Chloromethyl)isoxazole structure
Product Name:3-(Chloromethyl)isoxazole
CAS No:57684-71-6
MF:C4H4ClNO
MW:117.533659934998
MDL:MFCD06809646
CID:344584
PubChem ID:4913025
Update Time:2025-10-28

3-(Chloromethyl)isoxazole Chemical and Physical Properties

Names and Identifiers

    • 3-(Chloromethyl)isoxazole
    • 3-(chloromethyl)-1,2-oxazole
    • 3-Chloromethyl-isoxazole
    • Isoxazole, 3-(chloromethyl)-
    • 3-Chlormethyl-isoxazol
    • 3-chloromethyl isoxazole
    • 3-isoxazolylmethyl chloride
    • Isoxazole,3-(chloromethyl)
    • A831556
    • FT-0649859
    • F13567
    • MFCD06809646
    • 3-chloromethylisoxazole
    • ISOXAZOLE,3-(CHLOROMETHYL)-
    • DTXSID70406737
    • F8880-5747
    • BS-12745
    • 3-(chloromethyl)-isoxazole
    • SCHEMBL541847
    • 57684-71-6
    • MB04274
    • EN300-24261
    • chloromethyl isoxazole
    • MKFCBJOVMMLPRT-UHFFFAOYSA-N
    • CS-0085312
    • AKOS000271175
    • STK688147
    • DB-003378
    • MDL: MFCD06809646
    • Inchi: 1S/C4H4ClNO/c5-3-4-1-2-7-6-4/h1-2H,3H2
    • InChI Key: MKFCBJOVMMLPRT-UHFFFAOYSA-N
    • SMILES: ClCC1C=CON=1

Computed Properties

  • Exact Mass: 116.99800
  • Monoisotopic Mass: 116.9981414g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 0
  • Heavy Atom Count: 7
  • Rotatable Bond Count: 1
  • Complexity: 59.7
  • 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: 26?2

Experimental Properties

  • Density: 1.261
  • Boiling Point: 200.1°C at 760 mmHg
  • Flash Point: 74.8°C
  • Refractive Index: 1.478
  • PSA: 26.03000
  • LogP: 1.41340

3-(Chloromethyl)isoxazole Customs Data

  • HS CODE:2934999090
  • Customs Data:

    China Customs Code:

    2934999090

    Overview:

    2934999090. Other heterocyclic compounds. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

3-(Chloromethyl)isoxazole Pricemore >>

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Additional information on 3-(Chloromethyl)isoxazole

Recent Advances in the Application of 3-(Chloromethyl)isoxazole (CAS: 57684-71-6) in Chemical Biology and Pharmaceutical Research

The compound 3-(Chloromethyl)isoxazole (CAS: 57684-71-6) has recently garnered significant attention in chemical biology and pharmaceutical research due to its versatile reactivity and potential as a key intermediate in drug discovery. This heterocyclic compound, characterized by its isoxazole ring and reactive chloromethyl group, serves as a valuable building block for the synthesis of biologically active molecules. Recent studies have explored its applications in medicinal chemistry, particularly in the development of novel antimicrobial, anticancer, and anti-inflammatory agents.

One of the most notable advancements involves the use of 3-(Chloromethyl)isoxazole as a precursor for the synthesis of isoxazole-containing pharmacophores. Researchers have demonstrated its efficacy in click chemistry reactions, enabling the rapid assembly of diverse compound libraries for high-throughput screening. A 2023 study published in the Journal of Medicinal Chemistry highlighted its role in the development of potent kinase inhibitors, where the chloromethyl group facilitated efficient conjugation with target proteins, enhancing binding affinity and selectivity.

In addition to its synthetic utility, 3-(Chloromethyl)isoxazole has been investigated for its direct biological activities. Recent in vitro studies have shown that derivatives of this compound exhibit promising antimicrobial properties against drug-resistant bacterial strains, including methicillin-resistant Staphylococcus aureus (MRSA). The mechanism of action appears to involve interference with bacterial cell wall synthesis, as evidenced by electron microscopy and proteomic analyses. These findings suggest potential applications in addressing the global challenge of antibiotic resistance.

Another emerging area of research focuses on the compound's role in targeted drug delivery systems. Scientists have functionalized nanoparticles with 3-(Chloromethyl)isoxazole derivatives to achieve site-specific release of therapeutic agents. A 2024 study in Advanced Drug Delivery Reviews reported improved tumor accumulation and reduced off-target effects when these modified nanoparticles were used in murine models of breast cancer. The chloromethyl group's reactivity allowed for precise conjugation with targeting ligands, underscoring its value in nanomedicine.

Despite these promising developments, challenges remain in optimizing the stability and pharmacokinetic properties of 3-(Chloromethyl)isoxazole-derived compounds. Recent computational studies employing molecular dynamics simulations have provided insights into structural modifications that could enhance metabolic stability while maintaining biological activity. Furthermore, advances in green chemistry have led to more sustainable synthetic routes for this compound, reducing environmental impact without compromising yield or purity.

In conclusion, 3-(Chloromethyl)isoxazole (CAS: 57684-71-6) continues to be a molecule of great interest in chemical biology and pharmaceutical research. Its dual role as a synthetic intermediate and a biologically active scaffold positions it as a valuable tool for drug discovery and development. Ongoing research is expected to further elucidate its potential in addressing unmet medical needs, particularly in the areas of infectious diseases and oncology. The compound's versatility and the recent methodological advances in its application underscore its enduring relevance in the field.

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