97% Purity Ethyl 3-oxo-4-phenylbutanoate CAS 718-08-1

CAS Number:​​ 718-08-1

​Molecular Formula:​​ C₁₂H₁₄O₃

​Molecular Weight:​​ 206.24 g/mol

​IUPAC Name:​​ Ethyl 4-phenyl-3-oxobutanoate

​Synonyms:​​

Ethyl benzylacetoacetate

Ethyl 4-phenyl-3-oxobutyrate

3-Oxo-4-phenylbutanoic acid ethyl ester

​Physical State:​​ Colorless to pale yellow liquid

​Boiling Point:​​ ~150–155 °C at 12 mmHg (may vary with purity)

​Density:​​ ~1.1 g/cm³ at 20 °C

​Refractive Index:​​ n20/D ~1.51–1.515

Solubility:​​ Soluble in common organic solvents (e.g., ethanol, ethyl acetate, dichloromethane, acetone); insoluble in water.

​Stability:​​ Stable under normal storage conditions but may decompose under strong oxidizing or reducing conditions. Should be protected from moisture and stored in a cool, dry place.

​Characteristic:​​ Exhibits keto-enol tautomerism typical of β-keto esters.

​Pharmacological Role:​​ Primarily used as a synthetic intermediate; not typically employed as an active pharmaceutical ingredient itself.

​Biological Relevance:​​ Serves as a precursor for compounds with potential biological activities, such as:

       ​Antihypertensive agents​ (e.g., in the synthesis of certain ACE inhibitors or related heterocycles)

       Anti-inflammatory or analgesic compounds​ (via conversion to pyrazole or isoxazole derivatives)

       ​Chiral intermediates​ for drugs like statins (cholesterol-lowering agents) after further chemical modification.

​Toxicity:​​ Limited specific data, but β-keto esters generally require careful handling. May cause irritation to skin, eyes, and respiratory system. Standard laboratory precautions (gloves, goggles, ventilation) are recommended.

​Natural Occurrence:​​ Not known as a natural product; it is a synthetic compound.

​Laboratory/Industrial Synthesis:​​ Typically prepared via:

​1.Claisen condensation​ of ethyl acetoacetate with benzyl halides in the presence of a base (e.g., sodium ethoxide).

2.Alternative methods may involve acylation of phenylacetone with diethyl carbonate or transesterification approaches.

​Biosynthetic Pathways (in engineered systems):​​ Not common, but theoretically feasible via metabolic engineering of microbial pathways (e.g., using ketoacid and CoA intermediates), though not commercially practiced for this compound.

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​Q1: What is the primary use of ethyl 3-oxo-4-phenylbutanoate?​​

A1: It is mainly used as a chemical intermediate in the synthesis of pharmaceuticals (especially antihypertensive and anti-inflammatory drugs) and fine chemicals.

​Q2: How should this compound be stored?​​

A2: Store in a tightly sealed container, under an inert atmosphere (e.g., nitrogen), in a cool, dry place away from light and moisture. Recommended temperature: 2–8 °C for long-term storage.

​Q3: Is it hazardous?​​

A3: It may cause skin/eye irritation and respiratory discomfort. Always refer to the Safety Data Sheet (SDS) for specific hazards and handling instructions. Use personal protective equipment (PPE) and work in a fume hood.

​Q4: Can it be used in asymmetric synthesis?​​

A4: Yes, the chiral center at the 4-position (if introduced) or the prochiral ketone allows for asymmetric transformations, e.g., enzymatic reductions or chiral catalyst-mediated reactions.

​Q5: What are common impurities in commercial samples?​​

A5: Possible impurities include starting materials (ethyl acetoacetate, benzyl halides), decarboxylation products, or enol isomers. Purity is typically ≥95% (GC/HPLC), with higher grades available.

​Q6: Where can I find spectral data (NMR, IR, MS)?​​

A6: Spectral data are often available in commercial catalogs (e.g., Sigma-Aldrich, TCI) or databases like SciFinder, Reaxys, or NIST.

​Q7: Is it compatible with green chemistry protocols?​​

A7: Yes, it has been used in studies involving solvent-free reactions, biocatalysis, and recyclable catalysts to improve sustainability.

​Q8: What are typical packaging options?​​

A8: Available from milligram to kilogram quantities, often in glass bottles or metal cans for larger volumes. Custom packaging may be available from suppliers.