Verified laboratory-grade reference chemicals, peptides, and pharmaceutical intermediates manufactured under stringent ISO 9001 and cGMP compliant factory oversight.
An in-depth chemical evaluation of CAS 718-08-1: the multi-functional β-keto ester linchpin supporting modern stereoselective synthesis and heterocycle construction.
Ethyl 3-oxo-4-phenylbutanoate (also commonly identified across industrial manifests as Ethyl 4-phenylacetoacetate, Ethyl benzylacetoacetate, or Benzylacetoacetic acid ethyl ester, Formula: C12H14O3, Molecular Weight: 206.24 g/mol) is an essential organic intermediate possessing a chemically versatile β-dicarbonyl framework flanked by a mobile phenyl ring.
The acidic central methylene group positioned between the ester carbonyl and the ketone functionality enables rapid keto-enol tautomerism. This property dictates both its nucleophilic reactivity at the C2 position and its capacity to form stable, highly reactive bidentate metal chelates for catalytic condensation reactions.
Industrial chemists leverage the prochiral ketone at position 3 for stereoselective biocatalytic reduction (via engineered ketoreductases) and Noyori-type asymmetric hydrogenation (using Ru-BINAP complexes), giving access to enantiopure ethyl (3R)- or (3S)-3-hydroxy-4-phenylbutanoate at >99.5% optical purity.
| Analytical Parameter | Certified Standard Specification | Typical Factory Lot Analysis | Test Protocol / Instrument |
|---|---|---|---|
| Appearance | Clear, colorless to light pale yellow oily liquid | Conforms (Colorless, transparent) | Visual Inspection / Lovibond Scale |
| Chemical Assay (Purity) | ≥ 98.5% (Area Normalization) | 99.2% – 99.6% | Gas Chromatography (GC-FID) |
| Refractive Index (nD20) | 1.5110 – 1.5160 | 1.5135 | Abbe Refractometer (ASTM D1218) |
| Moisture Content (Karl Fischer) | ≤ 0.20% w/w | 0.06% w/w | Coulometric Titration (USP <921>) |
| Residual Solvents (Ethanol, Toluene) | ≤ 0.10% Individual / ≤ 0.50% Total | Below Detection Limits (ND) | Headspace GC-MS (ICH Q3C Class 2/3) |
| Specific Gravity (d25/25) | 1.080 – 1.095 g/cm³ | 1.088 g/cm³ | Digital Density Meter (ASTM D4052) |
Transforming complex bench-scale organic synthesis into high-throughput, atom-economical industrial operations with zero-runaway thermal guarantees.
Condensation of ethyl phenylacetate with anhydrous ethyl acetate in the presence of strong bases (such as sodium ethoxide or sodium hydride). Modern facilities optimize stoichiometric dosing in aprotic media to prevent self-condensation of phenylacetate, raising reaction selectivity from historical 72% baselines to modern yields in excess of 88%.
Phenylacetyl chloride coupling with Meldrum’s acid (2,2-dimethyl-1,3-dioxane-4,6-dione) followed by ethanol-mediated solvolysis and thermal decarboxylation. While requiring precise temperature dampening below -5°C during the acylation phase, this route yields exceptionally pure products devoid of high-boiling ester oligomers.
Leading factories have transitioned from legacy batch-stirred tank reactors (STR) to continuous micro-channel reactors. This eliminates exothermic thermal spikes during base-mediated proton abstraction, cuts residence time from 14 hours to 90 seconds, and drastically lowers total energy usage per metric ton produced.
Strategic procurement analysis detailing supply corridors, price sensitivities, regulatory trade barriers, and shipping stability parameters.
China (notably Jiangsu, Shandong, and Hebei chemical industrial clusters) remains the dominant manufacturing epicenter, providing access to low-cost raw precursors including benzyl chloride and diethyl malonate derivatives. Modern facilities here adhere to strict zero liquid discharge (ZLD) norms.
Western procurement teams focus heavily on vendor qualification, supply security, and REACH compliance dossiers. High demand from CDMOs scaling proprietary CNS drugs and specialized cardiovascular APIs has driven multi-year supply contracts with strict specifications on residual trace halides.
Exported globally under Harmonized System (HS) code 2918.30.00 (Carboxylic acids with ketone functionality). Material is packaged under inert nitrogen blankets in UN-approved 200L fluorinated HDPE drums or 1000L IBC totes, ensuring 24-month stability without hydrolysis under ambient marine freight.
Factory partnerships emphasize transparent audit rights, dual-sourcing contingency protocols, guaranteed safety stock warehouses in Rotterdam and Chicago, and comprehensive analytical lot verification to safeguard downstream manufacturing schedules.
Exploring the precise synthetic utility of Ethyl 3-oxo-4-phenylbutanoate across critical life-science manufacturing disciplines.
Serves as a fundamental bifunctional synthon for condensation with hydrazines, amidines, and diamines, creating diverse pyrazoles, pyrimidines, and quinolines. These heterocyclic rings form the pharmacophoric core of antipyretic, anti-inflammatory, and selective neuro-receptor antagonist pharmaceutical therapies.
Within crop science manufacturing, this β-keto ester functions as a direct synthetic intermediate for novel broad-spectrum strobilurin analogues and heterocyclic carboxylate fungicides, providing plant protection against ascomycetes and basidiomycetes in commercial agriculture.
Hydrolytic decarboxylation or alpha-functionalization gives access to specialty floral-balsamic fragrance components. Its high boiling stability makes it a valued intermediate for long-lasting olfactory fixatives and high-end cosmetic formulations requiring non-irritating, low-volatility aromatics.
Under catalytic stereoselective hydrogenation (using chiral ruthenium or rhodium diphosphine complexes), it provides optical access to Ethyl (R)-3-hydroxy-4-phenylbutanoate, an essential chiral building block for pharmaceutical NEP/ACE inhibitors and next-generation antihypertensive medications.
The enolate ion acts as an efficient oxygen-donor bidentate ligand capable of chelating transition metals (Cu, Fe, Ni, Zn). These organometallic complexes serve as selective catalysts for olefin polymerization and fine-chemical oxidation reactions.
Ensuring complete batch traceability, environmental stewardship, and full regulatory transparency for corporate compliance audits.
Every industrial delivery is accompanied by an authenticated Certificate of Analysis containing original GC-FID chromatograms, 1H/13C NMR spectral identity confirmations, Karl Fischer titration sheets, and residual solvent quantification via HS-GC-MS.
Pre-registered and fully registered dossiers are maintained for European Union imports under REACH Regulation (EC 1907/2006). Verified listed status on the US Toxic Substances Control Act (TSCA) inventory facilitates frictionless cross-border distribution.
Production facilities operate under ISO 14001 Environmental Management Systems. All synthetic lines feature closed-loop solvent reclamation units capturing >96% of organic volatiles, coupled with biological oxidation scrubbers to eliminate fugitive organic emissions.
Pioneering advancements across biocatalysis, automated flow chemistry, and decarbonized chemical manufacturing facilities.
Developing whole-cell transaminase enzyme platforms to convert the 3-oxo position directly into chiral unnatural beta-amino esters under aqueous, room-temperature conditions without toxic metal catalysts.
Piloting solvent-free, sacrificial-anode electrochemical cross-coupling of ethyl bromoacetate with phenylacetyl derivatives, slashing toxic salt byproducts by up to 82%.
Integrating in-line Fourier Transform Infrared (FTIR) and Raman spectrometry linked with deep-learning neural controllers to instantly adjust feed rates and heat exchange in real-time.
Transitioning factory steam generation to biomass gasification and green hydrogen thermal systems, aiming for full zero-emission intermediate manufacturing across our supply network by 2030.
Detailed technical guidance addressing the common chromatographic, logistical, and storage queries raised by corporate procurement officers and quality assurance auditors.
Explore our certified catalog of active ingredients, metabolic peptide analogues, and intermediate building blocks ready for dispatch.
