838-57-3

Basic information

• Product Name: ETHYL 4-NITROBENZOYLACETATE
• Synonyms: ETHYL P-NITROBENZOYLACETATE;ETHYL 4-NITROBENZOYLACETATE;ETHYL 3-(4-NITROPHENYL)-3-OXOPROPANOATE;ETHYL 3-OXO-3-(P-NITROPHENYL)PROPIONATE;ETHYL 2-(4-NITROBENZOYL) ACETATE;LABOTEST-BB LT00847933;AKOS BC-0951;4-NITROBENZOYLACETIC ACID ETHYL ESTER
• CAS NO: 838-57-3
• Molecular Formula: C₁₁H₁₁NO₅
• Molecular Weight: 237.21
• EINECS: 212-656-7
• Product Categories: Aromatic Esters;Benzoic acid;C10 to C11;Carbonyl Compounds;Esters
• Mol File: 838-57-3.mol
• Article Data: 41

Chemical Properties

• Melting Point: 67-71 °C
• Boiling Point: 379.74°C (rough estimate)
• Flash Point: 149.6 °C
• Appearance: yellow crystalline powder
• Density: 1.3350 (rough estimate)
• Vapor Pressure: 6.49E-05mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.70±0.25(Predicted)
• BRN: 1124763
• CAS DataBase Reference: ETHYL 4-NITROBENZOYLACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 4-NITROBENZOYLACETATE(838-57-3)
• EPA Substance Registry System: ETHYL 4-NITROBENZOYLACETATE(838-57-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37-26
• WGK Germany: 2
• RTECS: AJ1073500
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 838-57-3(Hazardous Substances Data)

Usage

Description

ETHYL 4-NITROBENZOYLACETATE is a yellow fine crystalline powder that serves as a versatile reactant in various chemical synthesis processes.

Uses

Used in Organic Synthesis:
ETHYL 4-NITROBENZOYLACETATE is used as a reactant for the synthesis of β-1,3-dicarbonyl aldehydes via oxidation, enabling the creation of complex organic molecules for various applications.
Used in Knoevenagel Condensation:
In the fine chemical industry, ETHYL 4-NITROBENZOYLACETATE is used as a reactant in Knoevenagel condensation using a lysine catalyst, facilitating the formation of valuable intermediates for pharmaceutical and agrochemical products.
Used in the Synthesis of Trisubstituted Furans:
ETHYL 4-NITROBENZOYLACETATE is utilized as a reactant in cycloisomerization reactions, contributing to the synthesis of trisubstituted furans, which are important building blocks in organic chemistry.
Used in Fluorination Reactions:
ETHYL 4-NITROBENZOYLACETATE is used as a reactant in fluorination processes using HF and iodosylbenzene, allowing for the introduction of fluorine atoms into organic compounds, which can significantly alter their properties.
Used in Intramolecular Michael Addition Reactions:
In the synthesis of benzylbutyrolactones, ETHYL 4-NITROBENZOYLACETATE is used as a reactant in intramolecular Michael addition reactions, providing a route to create diverse heterocyclic compounds.
Used in the Synthesis of Diols:
ETHYL 4-NITROBENZOYLACETATE is used as a reactant in the synthesis of diols via the reduction of aromatic and aliphatic keto esters, offering a method to produce important intermediates in the pharmaceutical and chemical industries.
Used in Cross-Coupling Reactions:
In the field of organic chemistry, ETHYL 4-NITROBENZOYLACETATE is used as a reactant in cross-coupling reactions for the stereoselective synthesis of unsymmetrical 1,4-enediones, which are valuable intermediates in the synthesis of natural products and pharmaceuticals.

InChI:InChI=1/C11H11NO5/c1-2-17-11(14)7-10(13)8-3-5-9(6-4-8)12(15)16/h3-6H,2,7H2,1H3

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 555-16-8 4-nitrobenzaldehdye 
• 64-17-5 ethanol 
• 29285-16-3 3-(4-nitrophenyl)-3-oxopropanoic acid 
• 13557-37-4 ethyl-2-(4-nitrobenzoyl)-3-oxobutanoate 
• 106353-52-0 3,3-Di-morpholin-4-yl-1-(4-nitro-phenyl)-propenone 
• 6148-64-7 ethyl potassium malonate 
• 122-04-3 4-nitro-benzoyl chloride 
• 105-36-2 ethyl bromoacetate 
• 100-19-6 (4-nitrophenyl)ethanone 
• 105-58-8 Diethyl carbonate 
• 7664-41-7 ammonia 
• 82961-74-8 5-[hydroxy(4-nitrophenyl)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 109-94-4 formic acid ethyl ester 

Downstream Products

• 100373-62-4 2,2-bis-hydroxymethyl-3-(4-nitro-phenyl)-3-oxo-propionic acid ethyl ester 
• 94259-00-4 5-[3-(4-nitro-phenyl)-3-oxo-propionylamino]-isophthalic acid dimethyl ester 
• 857948-38-0 3-(4-nitro-phenyl)-3-oxo-propionic acid-[2-(2,4-di-tert-pentyl-phenoxy)-anilide] 
• 53949-07-8 3-(4-nitro-phenyl)-2H-isoxazol-5-one 
• 61252-00-4 4-amino-β-oxobenzenepropanoic acid ethyl ester 
• 99843-62-6 3-(4-nitro-phenyl)-3-thioxo-propionic acid ethyl ester 
• 99983-34-3 ethyl 2-bromo-3-(4-nitrophenyl)-3-oxopropanoate 
• 109813-94-7 (4-Nitro-benzoyl)-phthalimino-essigsaeure-ethylester 
• 99-81-0 4-Nitrophenacyl bromide 
• 100-19-6 (4-nitrophenyl)ethanone 
• 1092-69-9 3-(4-nitrophenyl)-3-oxo-N-phenylpropanamide 
• 66838-68-4 2-(4'-Nitrobenzoylmethyl)benzothiazole 
• 2182-21-0 3-{2-[3-(4-nitro-phenyl)-3-oxo-propionylamino]-thiazol-4-yl}-benzenesulfonyl fluoride 
• 87591-76-2 6-Methyl-2-(4-nitro-phenyl)-pyrido[1,2-a]pyrimidin-4-one 

Relevant articles and documents

Annulation-retro-Claisen cascade of bifunctional peroxides for the synthesis of lactone natural products

A new and highly efficient annulation-retro-Claisen cascade, which involves the [4 + 1] or [5 + 1] annulation of α-benzoylacetates with bielectrophilic peroxides and a subsequent debenzoylation process under mild basic conditions, has been developed for the rapid construction of valuable tetrahydrofuran- and dihydropyran-2-carboxylates in good yields. By employing the new reaction, the unified total synthesis of γ- and δ-lactone natural products such as (±)-tanikolide, (±)-goniothalamins, (±)-7-epi-goniodiol, and (±)-plakolide A has been accomplished in 4-7 steps.

Electrochemical Oxidative Cyclization: Synthesis of Polysubstituted Pyrrole from Enamines

A conceptually novel method for the preparation of pyrrole is described by electrochemical-oxidation-induced intermolecular annulation via enamines. In a simple undivided cell, based on a sodium acetate-facilitated, polysubstituted pyrrole derivations has been facilely synthesized under external oxidant-free condition. This electrosynthetic approach providing an environmentally benign protocol for C?C bond cross-coupling and oxidative annulation, which features unparalleled broad scope of substrates and practicality.

Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes

Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine-or H2O2-induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.