• 1. Ligand-functionalized Pt nanoparticles as asymmetric heterogeneous catalysts: molecular reaction control by ligand–reactant interactions
  Anda ?ulce,Jana Backenk?hler,Imke Schrader,Massimo Delle Piane,Christian Müller,André Wark,Lucio Colombi Ciacchi,Vladimir Azov,Sebastian Kunz Catal. Sci. Technol. 2018 8 6062

• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Ketones
• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Ketones
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Comprehensive Overview of Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate (CAS No. 1999-00-4): Properties, Applications, and Industry Insights

Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate (CAS No. 1999-00-4) is a fluorinated organic ester with significant relevance in pharmaceutical and fine chemical synthesis. This compound, characterized by its 4-fluorophenyl moiety and β-ketoester functional group, serves as a versatile intermediate in the production of active pharmaceutical ingredients (APIs) and specialty chemicals. Its molecular structure, combining a fluorinated aromatic ring with an ester-linked oxopropanoate chain, enables unique reactivity patterns that are exploited in modern synthetic methodologies.

In recent years, the demand for fluorinated compounds like Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate has surged due to their enhanced metabolic stability and bioavailability in drug development. Researchers frequently search for "fluorophenyl ketoester applications" or "CAS 1999-00-4 synthesis methods," reflecting growing interest in its synthetic utility. The compound's electron-withdrawing fluorine substituent significantly influences its reactivity, making it valuable for Michael additions, Claisen condensations, and other carbon-carbon bond-forming reactions.

From a physicochemical perspective, Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate typically appears as a pale yellow to colorless liquid with a characteristic ester-like odor. Its molecular weight of 210.21 g/mol and balanced lipophilicity (logP ~1.8) make it suitable for various organic transformations. Analytical techniques such as HPLC, GC-MS, and NMR spectroscopy are commonly employed for purity assessment, with commercial samples often exceeding 97% purity.

The compound's applications extend beyond pharmaceuticals into materials science, where fluorinated building blocks are increasingly important. Industry professionals often inquire about "scaling up Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate production" or "green chemistry approaches for fluorinated esters," highlighting the intersection of synthetic efficiency and environmental considerations. Recent advances in continuous flow chemistry have demonstrated improved yields and reduced waste generation in the preparation of such β-ketoesters.

Quality control of CAS 1999-00-4 involves rigorous testing for residual solvents, heavy metals, and related substances. Regulatory compliance with ICH guidelines and REACH regulations ensures its safe handling and transportation. Storage recommendations typically include protection from moisture and oxidation under inert atmosphere at temperatures below 25°C to maintain stability.

Emerging research explores the compound's potential in catalyzed asymmetric synthesis, particularly in constructing chiral centers adjacent to fluorinated aromatic systems. This aligns with current trends in "stereoselective fluorination techniques" and "organofluorine building blocks" – topics generating substantial interest in medicinal chemistry forums. The 4-fluorophenyl group's unique electronic properties contribute to both the compound's reactivity and the biological activity of derived molecules.

Market analyses indicate steady growth for fluorinated intermediates like Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate, driven by expanding therapeutic areas requiring fluorine-containing compounds. Suppliers frequently list it under alternative identifiers such as "4-Fluorophenyl 3-oxobutanoate" or "ethyl 4-fluoro-β-ketobutyrate," emphasizing the importance of comprehensive search strategies when sourcing this material. Current Good Manufacturing Practice (cGMP) versions are available for pharmaceutical applications requiring stringent quality standards.

Environmental fate studies of 1999-00-4 demonstrate moderate biodegradability under aerobic conditions, with hydrolysis of the ester group being the primary degradation pathway. These findings inform waste management protocols and support the compound's classification as environmentally manageable when proper handling procedures are followed. The fluorine atom's persistence necessitates specific consideration in environmental risk assessments.

Innovative applications continue to emerge, including the compound's use in metal-organic framework (MOF) synthesis and fluorescent probe development. These cutting-edge applications leverage the fluorophenyl group's photophysical properties and coordination chemistry potential. Such developments answer frequent queries about "advanced materials from fluorinated ketoesters" and "CAS 1999-00-4 novel applications" in scientific literature.

The synthesis of Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate typically involves esterification of the corresponding β-ketoacid or Claisen-type condensation of ethyl acetate with 4-fluoroacetophenone. Process optimization focuses on yield improvement through parameters such as catalyst selection, reaction temperature, and solvent systems. Recent patent literature describes improved methods addressing common challenges like byproduct formation and purification difficulties.

Safety assessments indicate that standard organic laboratory precautions are sufficient for handling this material, with particular attention to avoid prolonged skin contact due to potential irritant properties. Safety Data Sheets (SDS) provide detailed guidance on personal protective equipment (PPE) requirements and first aid measures, reflecting industry best practices for similar organic esters.

As the pharmaceutical industry increasingly incorporates fluorine atoms into drug candidates, intermediates like Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate maintain strategic importance. Its combination of synthetic accessibility and versatile reactivity ensures continued relevance in both academic research and industrial applications, positioning it as a valuable tool in modern organic synthesis.

• 63131-29-3(Methyl 4-fluorobenzoylacetate)
• 1479-24-9(Ethyl 3-(2-fluorophenyl)-3-oxopropanoate)
• 252955-07-0(Ethyl 3-(3,4-Difluorophenyl)-3-oxopropanoate)
• 260246-17-1(methyl 3-(3-fluorophenyl)-3-oxopropanoate)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)