3-(Benzyl(methyl)amino)-1-phenylpropan-1-one: Properties & Uses
3-(Benzyl(methyl)amino)-1-phenylpropan-1-one: Properties & Uses
3-(Benzyl(methyl)amino)-1-phenylpropan-1-one is a β-aminoketone research intermediate featuring a phenyl-substituted propan-1-one backbone with a benzyl(methyl)amino side chain, making it a versatile building block for organic synthesis and pharmacological investigations.
- Product Name
- 3-(Benzyl(methyl)amino)-1-phenylpropan-1-one
- SKU
- B588181
- Compound Class
- β-Aminoketone (tertiary amine)
- Molecular Formula
- C17H19NO
- Molecular Weight
- 253.34 g/mol
- Key Functional Groups
- Ketone (C=O), tertiary amine (N-benzyl, N-methyl)
- Primary Application
- Organic synthesis intermediate and pharmacological research tool
Chemical Structure and Physicochemical Properties
3-(Benzyl(methyl)amino)-1-phenylpropan-1-one belongs to the class of β-aminoketones — compounds that bear an amino group at the β-carbon relative to a carbonyl. Its molecular formula is C17H19NO with a molecular weight of approximately 253.34 g/mol. The structure consists of a phenyl-substituted propan-1-one core, where the terminal carbon carries a tertiary amine formed by N-benzyl and N-methyl substituents.
The carbonyl group confers electrophilicity to the α-position and influences the compound's reactivity in condensation and reduction reactions. The tertiary amine nitrogen, flanked by a benzyl and a methyl group, provides a basic site (typical pKa of tertiary amines ~9–10 in water) and contributes to the lipophilicity of the molecule, influencing membrane permeability and solubility profiles relevant to biological screening.
Note: Specific physicochemical data such as melting point, boiling point, logP, and solubility values are not provided in the current source material and should be obtained from the supplier's certificate of analysis or verified literature. A review flag has been added accordingly.
Synthesis and Synthetic Utility
β-Aminoketones of this structural class are commonly prepared via Mannich-type reactions, wherein a ketone enolizable at the α-position is condensed with formaldehyde (or an equivalent aldehyde) and a secondary amine — in this case benzylmethylamine — to furnish the β-aminocarbonyl product. Alternatively, conjugate (Michael) addition of the secondary amine to an α,β-unsaturated ketone such as chalcone or benzalacetone derivatives represents another viable synthetic route.
As a synthetic intermediate, 3-(Benzyl(methyl)amino)-1-phenylpropan-1-one offers several handles for further elaboration: the ketone may be reduced to the corresponding amino alcohol, subjected to reductive amination, or engaged in condensation chemistry. The N-benzyl group can be removed by hydrogenolysis to unmask a secondary amine for downstream functionalization. These attributes make this compound useful in the preparation of more complex nitrogen-containing scaffolds relevant to medicinal chemistry programs.
Specific reaction yields, conditions, and literature precedents for this exact compound are not available in the source material; details should be confirmed against primary literature. A review flag has been added.
Research Applications
Compounds in the β-aminoketone family have attracted research interest across several domains. In medicinal chemistry, β-aminoketones serve as precursors to amino alcohols and cyclic amines, which are pharmacophores found in numerous bioactive molecules including adrenergic agents, local anesthetics, and CNS-active compounds. The phenylpropanone scaffold in particular has been explored in the context of adrenergic receptor pharmacology.
3-(Benzyl(methyl)amino)-1-phenylpropan-1-one may be employed as a building block in target-oriented synthesis, fragment-based drug discovery, or as a reference standard for analytical method development. Its well-defined tertiary amine and ketone functionalities also render it suitable as a model substrate for evaluating new catalytic methods, including asymmetric reduction and enantioselective amine synthesis.
Specific published biological activity data for this exact compound are not present in the source material. Any biological claims should be independently verified in peer-reviewed literature before use in research conclusions.
Handling, Storage, and Safety Considerations
As with most β-aminoketone research compounds, standard laboratory safety practices should be followed when handling 3-(Benzyl(methyl)amino)-1-phenylpropan-1-one. Personnel should wear appropriate personal protective equipment (PPE), including nitrile gloves, safety glasses, and a laboratory coat. Operations generating dust or aerosols should be conducted in a well-ventilated area or fume hood.
Storage conditions should be confirmed from the product's Safety Data Sheet (SDS) provided by Aladdin Scientific. In general, aminoketone compounds are stored in tightly sealed containers, away from moisture, heat, and incompatible oxidizing agents. Refrigerated storage (2–8 °C) or storage at room temperature under inert atmosphere may be recommended depending on stability data.
Specific GHS hazard classifications, LD50 values, and regulatory status for this compound are not available in the current source material. Researchers must consult the current SDS and applicable local regulations before use. A review flag has been added.
Frequently asked questions
What is the molecular formula and molecular weight of 3-(Benzyl(methyl)amino)-1-phenylpropan-1-one?
The molecular formula of 3-(Benzyl(methyl)amino)-1-phenylpropan-1-one is C17H19NO, with a molecular weight of approximately 253.34 g/mol. Researchers should confirm exact values against the certificate of analysis supplied with each lot.
What are the recommended storage conditions for this compound?
Specific storage conditions should be confirmed from the Safety Data Sheet (SDS) and certificate of analysis provided by Aladdin Scientific at the time of purchase. Generally, β-aminoketone compounds are stored in sealed containers away from moisture and heat; refrigerated storage under an inert atmosphere is commonly recommended for long-term stability.
How can I order 3-(Benzyl(methyl)amino)-1-phenylpropan-1-one from Aladdin Scientific?
This compound is available from Aladdin Scientific under SKU B588181. You can place an order directly through the Aladdin Scientific website or by contacting the sales team. Procurement staff should reference SKU B588181 when submitting purchase orders to ensure correct product identification.
What synthetic routes are commonly used to prepare β-aminoketones like this compound?
β-Aminoketones are typically synthesized via Mannich-type reactions (condensation of a ketone, an aldehyde, and a secondary amine) or by Michael addition of a secondary amine to an α,β-unsaturated ketone. For 3-(Benzyl(methyl)amino)-1-phenylpropan-1-one, both approaches are conceptually applicable, though specific experimental procedures should be verified in primary literature.
Is 3-(Benzyl(methyl)amino)-1-phenylpropan-1-one suitable as a reference standard?
This compound may be used as a reference standard for analytical method development, including HPLC and mass spectrometry workflows, provided that its purity is confirmed via the certificate of analysis. Researchers should verify that the lot purity meets their analytical requirements before use in quantitative applications.
References
- Aladdin Scientific. Product listing: 3-(Benzyl(methyl)amino)-1-phenylpropan-1-one, SKU B588181. Aladdin Scientific Corp.
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed. Wiley-Interscience, 1992. (General reference for Mannich reaction and β-aminoketone chemistry.)
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed. Oxford University Press, 2012. (Textbook reference for Michael addition and aminoketone reactivity.)
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