Ethyl 3-oxo-4-phenylbutanoate CAS 718-08-1 (also known as ethyl 4-phenyl-3-oxobutanoate or ethyl benzylacetoacetate) is an organic compound belonging to the class of β-keto esters. It features both a ketone and an ester functional group, with a phenyl substituent at the 4-position. Its structure makes it a versatile building block in organic synthesis, particularly in pharmaceutical and fine chemical manufacturing.
Name :
Ethyl 3-oxo-4-phenylbutanoateCAS No. :
718-08-1MF :
C₁₂H₁₄O₃MW :
206.24Purity :
97%Appearance :
Colorless to pale yellow liquidChemical Properties
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.
Biological Activities
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.
Biosynthesis
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.
Applications
FAQs
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.
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