Ethyl 4-nitrobenzoylacetate
Ethyl 4-nitrobenzoylacetate (CAS: 838-57-3) is a versatile organic building block with the linear formula O₂NC₆H₄COCH₂CO₂C₂H₅ and a molecular weight of 237.21 g/mol. This ester and carbonyl compound plays a significant role as a reactant in various organic syntheses. It is frequently employed in the preparation of complex molecules, including aldehydes, furans, and diones, through reactions like Knoevenagel condensation, cycloisomerization, and cross-coupling.
- IUPAC
- (p-Nitrobenzoyl)acetic acid ethyl ester,Ethyl 3-oxo-3-(4-nitrophenyl)propanoate,NSC 62134
- Synonyms
- Ethyl 3-oxo-3-(4-nitrophenyl)propanoate(p-Nitrobenzoyl)acetic acid ethyl esterNSC 62134
Synthesis of β-1,3-dicarbonyl aldehydes
Ethyl 4-nitrobenzoylacetate serves as a key reactant in the oxidation processes leading to the formation of β-1,3-dicarbonyl aldehydes. This application is crucial for creating specific functional groups in organic intermediates.
Knoevenagel Condensation Reactions
Utilising a lysine catalyst, this compound participates effectively in Knoevenagel condensation reactions. This enables the carbon-carbon bond formation necessary for building more complex organic structures.
Synthesis of Trisubstituted Furans
The compound is employed in cycloisomerization reactions, a vital pathway for the synthesis of trisubstituted furans. These heterocyclic compounds are important motifs in medicinal chemistry and materials science.
Fluorination Reactions
Ethyl 4-nitrobenzoylacetate can undergo fluorination when treated with reagents such as HF and iodosylbenzene. This process is essential for introducing fluorine atoms into organic molecules, often altering their properties.
Intramolecular Michael Additions
This ester is involved in intramolecular Michael addition reactions, which are instrumental in synthesising benzylbutyrolactones. These lactone structures are found in various natural products and pharmaceuticals.
Reduction to Diols
The reduction of Ethyl 4-nitrobenzoylacetate leads to the formation of diols. This transformation is applicable to both aromatic and aliphatic ketos esters, providing access to valuable alcohol functionalities.
| Molecular weight | 237.21 |
|---|---|
| Linear formula | O2NC6H4COCH2CO2C2H5 |
| Application | Reactant involved in:• Synthesis of β-1,3-dicarbonyl aldehydes via oxidation1• Knoevenagel condensation using a lysine catalyst2• Cycloisomerization fo rthe synthesis of trisubstituted furans3• Fluorination by HF and iodosylbenzene4• Intramolecular Michael addition reactions for synthesis of benzylbutyrolactones5• Synthesis of diols via reduction of aromatic and aliphatic ketos esters6• Cross-coupling reactions for stereoselective synthesis of unsymmetrical 1,4-enediones7 |
| Melting point | 71-73 °C(lit.) |
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is Ethyl 4-nitrobenzoylacetate used for?
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Ethyl 4-nitrobenzoylacetate is used as a reactant in organic synthesis. Its applications include the synthesis of β-1,3-dicarbonyl aldehydes, Knoevenagel condensation, cycloisomerization to furans, fluorination, intramolecular Michael additions for benzylbutyrolactones, reduction to diols, and cross-coupling reactions for 1,4-enediones.
What are the CAS number and molecular formula for Ethyl 4-nitrobenzoylacetate?
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The CAS number for Ethyl 4-nitrobenzoylacetate is 838-57-3. Its linear formula is O₂NC₆H₄COCH₂CO₂C₂H₅.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this chemical as a technical/research grade material. We do not represent it as USP, BP, or EP grade.
What are the safety and handling precautions for Ethyl 4-nitrobenzoylacetate?
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Ethyl 4-nitrobenzoylacetate is classified under GHS hazards. Please consult the Safety Data Sheet (SDS) for comprehensive information on handling, storage, and appropriate personal protective equipment. It is classified as hazardous in Germany (WGK 2).
How is this chemical packed, shipped, and exported?
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Tech Serve Solutions, a specialist global supplier and exporter, carefully packs and ships chemicals according to international regulations to ensure safe and compliant delivery worldwide.
How can I request a sample or quote for Ethyl 4-nitrobenzoylacetate?
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To request a sample or a quotation, please contact our sales department through the website or by phone, providing the product name and CAS number (838-57-3).
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