Cas no 32249-37-9 (ethyl 3-(1-methylcyclopropyl)-3-oxopropanoate)

Ethyl 3-(1-methylcyclopropyl)-3-oxopropanoate is a specialized ester compound featuring a 1-methylcyclopropyl ketone moiety. Its unique structure, combining a cyclopropyl ring with a β-ketoester functionality, makes it a valuable intermediate in organic synthesis. The compound is particularly useful in the preparation of cyclopropane-containing derivatives, which are of interest in pharmaceutical and agrochemical research due to their enhanced metabolic stability and steric constraints. The ethyl ester group enhances solubility in organic solvents, facilitating further transformations such as alkylations or condensations. This compound’s stability under mild conditions and reactivity toward nucleophiles make it a versatile building block for constructing complex molecular frameworks.
ethyl 3-(1-methylcyclopropyl)-3-oxopropanoate structure
32249-37-9 structure
Product Name:ethyl 3-(1-methylcyclopropyl)-3-oxopropanoate
CAS No:32249-37-9
MF:C9H14O3
MW:170.205663204193
MDL:MFCD23870411
CID:4646030
PubChem ID:10866760
Update Time:2025-10-31

ethyl 3-(1-methylcyclopropyl)-3-oxopropanoate Chemical and Physical Properties

Names and Identifiers

    • ethyl 3-(1-methylcyclopropyl)-3-oxopropanoate
    • 32249-37-9
    • DTXSID601266502
    • ethyl3-(1-methylcyclopropyl)-3-oxopropanoate
    • F95476
    • Z1395254572
    • DB-198157
    • AKOS018865209
    • IWHYFYBVTHEJLL-UHFFFAOYSA-N
    • Ethyl 1-methyl-I(2)-oxocyclopropanepropanoate
    • ethyl (1-methylcyclopropanecarbonyl)acetate
    • SCHEMBL4414359
    • EN300-202746
    • MDL: MFCD23870411
    • Inchi: 1S/C9H14O3/c1-3-12-8(11)6-7(10)9(2)4-5-9/h3-6H2,1-2H3
    • InChI Key: IWHYFYBVTHEJLL-UHFFFAOYSA-N
    • SMILES: O=C(CC(=O)OCC)C1(C)CC1

Computed Properties

  • Exact Mass: 170.094294304g/mol
  • Monoisotopic Mass: 170.094294304g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 12
  • Rotatable Bond Count: 5
  • Complexity: 204
  • 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: 1.2
  • Topological Polar Surface Area: 43.4?2

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Additional information on ethyl 3-(1-methylcyclopropyl)-3-oxopropanoate

Comprehensive Analysis of Ethyl 3-(1-methylcyclopropyl)-3-oxopropanoate (CAS No. 32249-37-9)

Ethyl 3-(1-methylcyclopropyl)-3-oxopropanoate (CAS No. 32249-37-9) is a versatile organic compound widely utilized in pharmaceutical intermediates, fragrance synthesis, and specialty chemical applications. Its unique cyclopropyl and ester functional groups make it a valuable building block in modern organic chemistry. With the growing demand for high-purity intermediates in drug development, this compound has gained significant attention from researchers and manufacturers alike.

The molecular structure of ethyl 3-(1-methylcyclopropyl)-3-oxopropanoate features a 1-methylcyclopropyl moiety attached to a β-ketoester framework. This configuration provides exceptional reactivity for Michael additions, cyclization reactions, and other transformations crucial for creating complex molecular architectures. Recent studies highlight its potential in developing bioactive molecules, particularly in the synthesis of flavors and fragrances with improved stability profiles.

In the context of green chemistry trends, researchers are exploring more sustainable production methods for CAS 32249-37-9. The compound's compatibility with enzymatic catalysis and microwave-assisted synthesis aligns with current industry priorities for eco-friendly manufacturing. Analytical techniques like GC-MS and HPLC are routinely employed to ensure the compound meets the stringent purity requirements of pharmaceutical-grade applications.

The global market for specialty esters like ethyl 3-(1-methylcyclopropyl)-3-oxopropanoate is expanding rapidly, driven by increased R&D investment in custom synthesis services. Formulators value this compound for its balanced lipophilicity and steric properties, which enable precise modulation of molecular characteristics in target applications. Storage typically requires protection from moisture and oxidation, with recommended conditions below 25°C in argon-filled containers.

Recent patent literature reveals innovative applications of 32249-37-9 in agrochemicals and material science. The methylcyclopropyl group's conformational restriction proves particularly valuable when designing compounds with enhanced target specificity. Quality control protocols emphasize rigorous testing for isomeric purity and residual solvents, as these factors critically impact performance in downstream reactions.

From a regulatory perspective, ethyl 3-(1-methylcyclopropyl)-3-oxopropanoate complies with major chemical inventories including TSCA and REACH. Manufacturers are increasingly adopting continuous flow chemistry approaches to improve yield and consistency of this intermediate. The compound's Knoevenagel condensation reactivity makes it particularly useful for constructing heterocyclic scaffolds prevalent in modern medicinal chemistry.

Analytical data for CAS 32249-37-9 typically shows characteristic NMR signals at 1.25 ppm (triplet, ester CH3), 3.45 ppm (singlet, cyclopropyl CH3), and 4.15 ppm (quartet, ester CH2). The carbonyl stretching frequency in IR spectroscopy appears around 1735 cm-1, confirming the ester functionality. These spectral features provide essential quality benchmarks for users performing structure verification.

In formulation science, the compound's logP value (approximately 1.8) indicates favorable membrane permeability characteristics, explaining its utility in prodrug design. Stability studies demonstrate excellent compatibility with common organic solvents including THF, dichloromethane, and ethyl acetate. However, prolonged exposure to strong bases should be avoided to prevent ester hydrolysis.

The synthesis of ethyl 3-(1-methylcyclopropyl)-3-oxopropanoate typically involves Claisen condensation of appropriate precursors, followed by careful purification via fractional distillation. Process chemists emphasize controlling the reaction exotherm during scale-up to maintain optimal regioselectivity. Recent process improvements have achieved yields exceeding 85% while reducing organic waste generation.

Emerging applications in electronic materials leverage the compound's ability to form conjugated systems through various cross-coupling reactions. Its volatility profile (bp ~215°C at 760 mmHg) makes it suitable for vapor deposition techniques in thin film production. These diverse applications underscore why 32249-37-9 remains a compound of significant interest across multiple industries.

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