Ethyl 4-nitrobenzoylacetate

Base Information

• Chemical Name: Ethyl 4-nitrobenzoylacetate
• CAS No.: 838-57-3
• Molecular Formula: C11H11 N O5
• Molecular Weight: 237.212
• Hs Code.: 29183000
• European Community (EC) Number: 212-656-7
• NSC Number: 62134
• UNII: E9KY7LH3TA
• DSSTox Substance ID: DTXSID9061201
• Nikkaji Number: J169.153H
• Wikidata: Q81989360
• Mol file: 838-57-3.mol

Synonyms:Ethyl 4-nitrobenzoylacetate;838-57-3;ethyl 3-(4-nitrophenyl)-3-oxopropanoate;Ethyl (p-nitrobenzoyl)acetate;Ethyl (4-nitrobenzoyl)acetate;(p-Nitrobenzoyl)acetic acid ethyl ester;(4-Nitrobenzoyl)acetic acid ethyl ester;ETHYL p-NITROBENZOYLACETATE;ethyl 3-oxo-3-(4-nitrophenyl)propanoate;Benzenepropanoic acid, 4-nitro-beta-oxo-, ethyl ester;Ethyl 4-nitro-beta-oxobenzenepropanoate;EINECS 212-656-7;NSC 62134;E9KY7LH3TA;ACETIC ACID, (p-NITROBENZOYL)-, ETHYL ESTER;BRN 1124763;NSC-62134;Benzenepropanoic acid, 4-nitro-.beta.-oxo-, ethyl ester;Ethyl 3-(4-Nitrophenyl)-3-oxopropionate;ethyl 3-(4-nitrophenyl)-3-oxo-propanoate;3-(4-nitrophenyl)-3-oxopropionic acid ethyl ester;4-10-00-02759 (Beilstein Handbook Reference);4-Nitrobenzoylacetic Acid Ethyl Ester;MFCD00007357;Maybridge1_002011;UNII-E9KY7LH3TA;ethyl-4-Nitrobenzoylacetate;Oprea1_250969;SCHEMBL276340;DTXSID9061201;HMS547D09;NSC62134;STK325361;AKOS000119352;AC-17238;AMY202100127;AS-19945;CS-0022845;FT-0626099;N0513;EN300-20198;4-Nitro-b-oxo-benzenepropanoic acid ethyl ester;F16294;4-Nitro-beta-oxo-benzenepropanoic acid ethyl ester;A840669;3-Oxo-3-(p-nitrophenyl)propionic acid, ethyl ester;F0787-0006;Z104477224

Chemical Property of Ethyl 4-nitrobenzoylacetate

Chemical Property:

• Appearance/Colour: yellow crystalline powder
• Vapor Pressure: 6.49E-05mmHg at 25°C
• Melting Point: 67-71 °C
• Refractive Index: 1.5300 (estimate)
• Boiling Point: 344.7 °C at 760 mmHg
• PKA: 8.70±0.25(Predicted)
• Flash Point: 149.6 °C
• PSA: 89.19000
• Density: 1.276 g/cm³
• LogP: 2.25390
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 237.06372245
• Heavy Atom Count: 17
• Complexity: 302

Purity/Quality:

97% ^*data from raw suppliers

Ethyl (4-Nitrobenzoyl)acetate >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)CC(=O)C1=CC=C(C=C1)[N+](=O)[O-]
• Uses: 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. 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

Technology Process of Ethyl 4-nitrobenzoylacetate

There total 35 articles about Ethyl 4-nitrobenzoylacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

diazoacetic acid ethyl ester (623-73-4) + 4-nitrobenzaldehdye (555-16-8) → ethyl 4-nitrobenzoylacetate (838-57-3)

Guidance literature:

With molybdenium(VI) dioxodichloride; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1055/s-2008-1067029

Reference yield: 91.0%

ethyl potassium malonate (6148-64-7) + 9-methyl-9H-fluorene-9-carbonyl chloride (82102-37-2) + para-nitrophenyl bromide (586-78-7) → ethyl 4-nitrobenzoylacetate (838-57-3)

Guidance literature:

With dichloro(1,5-cyclooctadiene)palladium(II); N-Methyldicyclohexylamine; triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; magnesium chloride; tri tert-butylphosphoniumtetrafluoroborate; In 1,4-dioxane; at 80 ℃; for 18h; Reagent/catalyst; Inert atmosphere; Glovebox;

DOI:10.1002/anie.201304072

Reference yield: 90.0%

ethanol (64-17-5) + 2,2-dimethyl-5-(4-nitrobenzoyl)-1,3-dioxane-4,6-dione (112378-39-9) → ethyl 4-nitrobenzoylacetate (838-57-3)

Guidance literature:

for 0.0833333h; microwave irradiation;

upstream raw materials:

diazoacetic acid ethyl ester

4-nitrobenzaldehdye

ethanol

3-(4-nitrophenyl)-3-oxopropanoic acid

Downstream raw materials:

2,2-bis-hydroxymethyl-3-(4-nitro-phenyl)-3-oxo-propionic acid ethyl ester

5-[3-(4-nitro-phenyl)-3-oxo-propionylamino]-isophthalic acid dimethyl ester

3-(4-nitro-phenyl)-3-oxo-propionic acid-[2-(2,4-di-tert-pentyl-phenoxy)-anilide]

3-(4-nitro-phenyl)-2H-isoxazol-5-one