52119-39-8

Basic information

• Product Name: ETHYL (2-NITROBENZOYL)ACETATE
• Synonyms: ETHYL (2-NITROBENZOYL)ACETATE;ETHYL 3-(2-NITROPHENYL)-3-OXOPROPANOATE;3-(2-NITRO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER;Ethyl 2-nitrobenzoylacetate 97%;ethyle2-nitrobenzoylacetate
• CAS NO: 52119-39-8
• Molecular Formula: C₁₁H₁₁NO₅
• Molecular Weight: 237.21
• Product Categories: C10 to C11;Carbonyl Compounds;Esters
• Mol File: 52119-39-8.mol
• Article Data: 12

Chemical Properties

• Melting Point: 30-34 °C(lit.)
• Boiling Point: 353.28 °C at 760 mmHg
• Flash Point: >230 °F
• Appearance: Clear orange to brown/Liquid
• Density: 1.277 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.542
• Storage Temp.: 2-8°C
• PKA: 9.42±0.46(Predicted)
• CAS DataBase Reference: ETHYL (2-NITROBENZOYL)ACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL (2-NITROBENZOYL)ACETATE(52119-39-8)
• EPA Substance Registry System: ETHYL (2-NITROBENZOYL)ACETATE(52119-39-8)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 52119-39-8(Hazardous Substances Data)

Usage

Uses

Ethyl 2-nitrobenzoylacetate may be used to synthesize ethyl 2-bromo-2′-nitrobenzoylacetate and 4-hydroxy-2(1H)-quinolone.

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

Upstream product

• 3740-52-1 2-(2-nitrophenyl)acetic acid 
• 2414-98-4 magnesium ethylate 
• 530-62-1 1,1'-carbonyldiimidazole 
• 366-18-7 [2,2]bipyridinyl 
• 1071-46-1 hydrogen ethyl malonate 
• 610-14-0 2-nitrobenzyl chloride 
• 552-16-9 ortho-nitrobenzoic acid 
• 6148-64-7 ethyl potassium malonate 
• 106718-56-3 diethyl 2-(2-nitro-benzoyl)malonate 
• 105-53-3 diethyl malonate 
• 22751-16-2 2-nitrobenzoylacetic acid 

Downstream Products

• 122022-06-4 2,5-dimethoxy(2-nitrobenzoyl)acetanilide 
• 67377-25-7 4-o-nitrophenyl-7-propargyloxy-coumarin 
• 1082832-09-4 3-(2-nitro-phenyl)-3-hydroxy-1-(4-phenyl-piperazin-1-yl)-propan-1-one 
• 1082832-07-2 4-[2-oxo-2-(4-phenyl-piperazin-1-yl)-ethyl]-1,4-dihydro-benzo[d][1,3]oxazin-2-one 
• 1338250-50-2 C₁₇H₁₈N₄O₅ 
• 1338250-51-3 C₁₈H₂₀N₄O₄ 
• 1338250-52-4 C₁₇H₂₀N₄O₄ 
• 1338250-53-5 C₁₅H₁₆N₄O₄ 
• 1338250-36-4 C₂₉H₂₅N₇O 
• 1338250-37-5 C₃₀H₂₇N₇O 
• 1338250-38-6 C₂₉H₂₄FN₇O 
• 1338250-39-7 C₂₉H₂₄ClN₇O 
• 1338250-40-0 C₃₀H₂₇N₇ 
• 1338250-41-1 C₃₁H₂₉N₇ 

Relevant articles and documents

Synthesis method and device of 4 -hydroxyquinoline -3 - formic acid

The invention relates to the technical field of medicine preparation, and particularly discloses a synthesis method and device of 4 -hydroxyquinoline -3 - formic acid, wherein o-nitrobenzoic acid and a monoethyl propionate potassium salt are condensed to obtain 3 - (2 - nitrophenyl) -3 - oxopropanoate. The ethyl powder is reacted with 3 - (2 - nitrophenyl) -3 - oxopropanoate to obtain 3 - (2 - aminophenyl) -3 - oxopropanoate. 3 - (2 - Aminophenyl) -3 - oxopropanoate was reacted with DMF-DMA and DMF via a closed loop to give 4 -hydroxyquinoline -3 - ethyl ester. The 4 -hydroxyquinoline -3 - formate was hydrolyzed under basic conditions to give 4 -hydroxyquinoline -3 - formic acid. 4 -hydroxyquinoline -3 - formic acid has the advantages of low cost, short reaction time and simple post-treatment in the synthesis process.

An Efficient Synthesis of Ivacaftor

New and practical synthetic route of ivacaftor is described on a grams scale. An electrophilic addition of two t-butyl groups to the aromatic ring is adopted to prepare 5-amino-2,4-di-t-butylphenol in 61% yield over three steps with 98.1% purity (high-performance liquid chromatography). An intramolecular cyclization of ethyl 3-(2-aminophenyl)-3-oxo-propanoate with dimethylformamide-dynamic mechanical analysis is used to prepare 4-oxo-1,4-dihydroquinoline-3-carboxylic acid in 54% yield over four steps. Ivacaftor is obtained by condensation of the two parts in 71% yield with 99.1% purity (high-performance liquid chromatography).

Expeditious synthesis of ivacaftor

An expeditious synthesis for Ivacaftor featuring modified Leimgruber-Batcho procedure was described. The overall yield is 39% over six steps from commercially available 2-nitrobenzoyl chloride.