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

Chemical Properties

yellow fine crystalline powder

Uses

Different sources of media describe the Uses of 838-57-3 differently. You can refer to the following data:
1. It is employed as a reactant involved in synthesis of β-1,3-dicarbonyl aldehydes via oxidation, knoevenagel condensation using a lysine catalyst, and cycloisomerization for the synthesis of trisubstituted furans. It is also a reactant for the fluorination by HF and iodosylbenzene, intramolecular Michael addition reactions and synthesis of diols. Also applied in the synthesis of diols via reduction of aromatic and aliphatic ketos esters6 and cross-coupling reactions for stereo selective synthesis of unsymmetrical 1,4-enediones.
2. Reactant involved in:Synthesis of β-1,3-dicarbonyl aldehydes via oxidationKnoevenagel condensation using a lysine catalystCycloisomerization fo rthe synthesis of trisubstituted furansFluorination by HF and iodosylbenzeneIntramolecular Michael addition reactions for synthesis of benzylbutyrolactonesSynthesis of diols via reduction of aromatic and aliphatic ketos estersCross-coupling reactions for stereoselective synthesis of unsymmetrical 1,4-enediones

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 
• 141-97-9 ethyl acetoacetate 
• 13361-47-2 1-(4-nitro-benzoyl)-1H-benzoimidazole 
• 7664-41-7 ammonia 

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 
• 15118-49-7 4-(4-nitrophenyl)-4-oxobutanoic acid 
• 1092-69-9 3-(4-nitrophenyl)-3-oxo-N-phenylpropanamide 
• 66838-68-4 2-(4'-Nitrobenzoylmethyl)benzothiazole 
• 101601-20-1 5-hydroxy-2-(4-nitro-phenyl)-benzofuran-3-carboxylic acid ethyl ester 

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.