Cas no 16882-23-8 (4-Methoxy-3-methylphenylacetone)

4-Methoxy-3-methylphenylacetone is a specialized organic compound featuring a methoxy-substituted phenylacetone structure with an additional methyl group at the 3-position. This compound is of interest in synthetic organic chemistry due to its utility as a key intermediate in the preparation of more complex molecules, particularly in pharmaceutical and fine chemical applications. Its distinct substitution pattern enhances reactivity and selectivity in various transformations, such as reductive amination or condensation reactions. The methoxy and methyl groups contribute to its stability and solubility in common organic solvents, facilitating handling and purification. Researchers value this compound for its versatility in constructing substituted phenethylamine derivatives.
4-Methoxy-3-methylphenylacetone structure
16882-23-8 structure
Product Name:4-Methoxy-3-methylphenylacetone
CAS No:16882-23-8
MF:C11H14O2
MW:178.227663516998
MDL:MFCD00210447
CID:121959
PubChem ID:18628084
Update Time:2025-05-23

4-Methoxy-3-methylphenylacetone Chemical and Physical Properties

Names and Identifiers

    • 4-Methoxy-3-methylphenylacetone
    • 1-(4-methoxy-3-methylphenyl)propan-2-one
    • 2-Propanone,1-(4-methoxy-3-methylphenyl)-
    • 1-(4-Methoxy-3-methylphenyl)-2-propanone
    • 2-Propanone, 1-(4-methoxy-3-methylphenyl)-
    • 2-Methyl-4-(2-oxopropyl)anisole
    • FCH832625
    • 8625AA
    • AX8098427
    • SCHEMBL4082027
    • 16882-23-8
    • A901270
    • DTXSID30595277
    • FT-0691913
    • N10857
    • EN300-1845414
    • AKOS006229915
    • DS-15377
    • MFCD00210447
    • SY244718
    • MDL: MFCD00210447
    • Inchi: 1S/C11H14O2/c1-8-6-10(7-9(2)12)4-5-11(8)13-3/h4-6H,7H2,1-3H3
    • InChI Key: QSBPLIJLGSKDTH-UHFFFAOYSA-N
    • SMILES: O(C)C1C=CC(=CC=1C)CC(C)=O

Computed Properties

  • Exact Mass: 178.09942
  • Monoisotopic Mass: 178.099379685g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 3
  • Complexity: 177
  • 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: 1.9
  • Topological Polar Surface Area: 26.3

Experimental Properties

  • Density: 1.011±0.06 g/cm3 (20 oC 760 Torr),
  • Boiling Point: 164-166 oC (10 Torr)
  • Flash Point: 106.7±16.7 oC,
  • Solubility: Slightly soluble (1.4 g/l) (25 o C),
  • PSA: 26.3

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abcr
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Additional information on 4-Methoxy-3-methylphenylacetone

Professional Introduction to 4-Methoxy-3-methylphenylacetone (CAS No. 16882-23-8)

4-Methoxy-3-methylphenylacetone, identified by the Chemical Abstracts Service Number (CAS No.) 16882-23-8, is a significant organic compound with a broad spectrum of applications in the field of chemical biology and pharmaceutical research. This compound, featuring a phenylacetone core structure with methoxy and methyl substituents, has garnered considerable attention due to its versatile reactivity and potential utility in synthetic chemistry, particularly in the development of biologically active molecules.

The molecular formula of 4-Methoxy-3-methylphenylacetone is C10H12O, reflecting its composition of 10 carbon atoms, 12 hydrogen atoms, and one oxygen atom. The presence of both a methoxy group (-OCH3) and a methyl group (-CH3) on the aromatic ring introduces unique electronic and steric properties, making it a valuable intermediate in various synthetic pathways. The compound exhibits moderate solubility in organic solvents such as ethanol, acetone, and dichloromethane, which facilitates its use in solution-phase reactions.

In recent years, 4-Methoxy-3-methylphenylacetone has been extensively studied for its role in the synthesis of pharmacologically relevant compounds. Its structural motif is frequently employed in the development of novel therapeutic agents, including those targeting neurological disorders, inflammatory conditions, and metabolic diseases. The methoxy group enhances the lipophilicity of the molecule, improving its membrane permeability and bioavailability—a critical factor in drug design.

One of the most compelling aspects of 4-Methoxy-3-methylphenylacetone is its utility as a precursor in the synthesis of more complex heterocyclic compounds. Researchers have leveraged its reactivity to construct fused ring systems, such as indoles and benzodiazepines, which are prevalent in many FDA-approved medications. The compound’s ability to undergo various transformations—such as oxidation, reduction, and nucleophilic substitution—makes it an indispensable tool for medicinal chemists seeking to explore new chemical spaces.

The latest advancements in computational chemistry have further highlighted the importance of 4-Methoxy-3-methylphenylacetone. Molecular modeling studies indicate that this compound can serve as a scaffold for designing molecules with enhanced binding affinity to biological targets. By integrating machine learning algorithms with traditional synthetic methodologies, researchers can predict optimal modifications to the structure of 4-Methoxy-3-methylphenylacetone, accelerating the discovery process for next-generation drugs.

Additionally, 4-Methoxy-3-methylphenylacetone has found applications in agrochemical research. Its derivatives exhibit promising activity against certain plant pathogens, offering a potential alternative to conventional pesticides. This dual utility—both in pharmaceuticals and agriculture—underscores the compound’s broad industrial relevance.

The synthesis of 4-Methoxy-3-methylphenylacetone typically involves Friedel-Crafts acylation followed by selective methylation or demethylation steps. Recent improvements in catalytic systems have enabled more efficient and environmentally benign routes to this intermediate. For instance, transition metal-catalyzed cross-coupling reactions now provide access to substituted phenylacetones with higher yields and fewer byproducts compared to traditional methods.

In academic research circles, 4-Methoxy-3-methylphenylacetone continues to be a subject of investigation due to its role as a key intermediate in natural product synthesis. Several studies have demonstrated its use in constructing analogs of bioactive molecules isolated from plants and microorganisms. These efforts not only expand our understanding of natural product chemistry but also contribute to the development of novel therapeutic strategies.

The safety profile of 4-Methoxy-3-methylphenylacetone is another area of interest. While it is not classified as hazardous under standard conditions, proper handling protocols must be followed to ensure worker safety. Storage should be conducted in cool, dry environments away from incompatible substances such as strong oxidizers. Furthermore, personal protective equipment (PPE) including gloves and safety goggles is recommended during handling.

Economic considerations also play a role in the industrial production of 4-Methoxy-3-methylphenylacetone. As demand for pharmaceutical intermediates grows, optimizing synthetic routes to reduce costs while maintaining quality becomes increasingly important. Collaborative efforts between academia and industry are driving innovation in this area, leading to more cost-effective and sustainable manufacturing processes.

The future prospects for 4-Methoxy-3-methylphenylacetone are bright, with ongoing research exploring new applications and synthetic methodologies. As our understanding of biological systems evolves, so too will the need for sophisticated intermediates like this one. Whether used to develop life-saving medications or advanced agricultural solutions, 4-Methoxy-3-methylphenylacetone remains a cornerstone of modern chemical research.

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