4-Nitrobenzyl acetoacetate

Base Information

• Chemical Name: 4-Nitrobenzyl acetoacetate
• CAS No.: 61312-84-3
• Molecular Formula: C11H11NO5
• Molecular Weight: 237.212
• Hs Code.: 2918300090
• European Community (EC) Number: 612-114-3
• DSSTox Substance ID: DTXSID90375411
• Nikkaji Number: J1.304.279I
• Wikidata: Q72495586
• Mol file: 61312-84-3.mol

Synonyms:61312-84-3;4-Nitrobenzyl acetoacetate;4-nitrobenzyl 3-oxobutanoate;(4-nitrophenyl)methyl 3-oxobutanoate;p-nitrobenzyl acetoacetate;Acetoacetic Acid 4-Nitrobenzyl Ester;Butanoic acid, 3-oxo-, (4-nitrophenyl)methyl ester;MFCD00799237;3-trifluoromethylpropionanilide;Acetoacetic acid 4-nitrobenzyl;SCHEMBL5765803;DTXSID90375411;KQPGVCMZXFBYMM-UHFFFAOYSA-N;AMY41282;(4-Nitrophenyl)methyl-3-oxobutanoate;AKOS015890400;CS-W012860;AS-15175;SY036167;FT-0640743;N0875;E78113;A833153

Chemical Property of 4-Nitrobenzyl acetoacetate

Chemical Property:

• Appearance/Colour: clear liquid
• Vapor Pressure: 7.21E-06mmHg at 25°C
• Melting Point: 45 °C
• Refractive Index: 1.542
• Boiling Point: 376.514 °C at 760 mmHg
• PKA: 10.08±0.46(Predicted)
• Flash Point: 170.471 °C
• PSA: 89.19000
• Density: 1.288 g/cm³
• LogP: 2.14030
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.6
• 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:

99% ^*data from raw suppliers

4-Nitrobenzyl Acetoacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)CC(=O)OCC1=CC=C(C=C1)[N+](=O)[O-]
• Uses: 4-Nitrobenzyl Acetoacetate acts as a reagent in the preparation of panipenem via esterification of nitrobenzyl alcohol followed by substitution, cyclizations and hydrogenation. Panipenem I is a new carbapenem antibiotic for the treatment of inflammation.

Technology Process of 4-Nitrobenzyl acetoacetate

There total 2 articles about 4-Nitrobenzyl acetoacetate 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: 90.0%

4-nitrobenzyl chloride (619-73-8) + acetoacetic acid methyl ester (105-45-3) → 4-nitrobenzyl 3-oxobutanoate (61312-84-3)

Guidance literature:

With copper ferrite; In toluene; for 8h; Reflux;

DOI:10.1039/c4ra15014g

Reference yield: 82.0%

4-nitrobenzyl chloride (619-73-8) + ethyl acetoacetate (141-97-9) → 4-nitrobenzyl 3-oxobutanoate (61312-84-3)

Guidance literature:

for 0.333333h; microwave irradiation;

DOI:10.1080/00397910008087215

Reference yield: 90.4%

4-nitrobenzyl 3-oxobutanoate (61312-84-3) → 4-nitrobenzyl 2-diazo-3-oxo-butanoate (82551-63-1)

Guidance literature:

With 4-toluenesulfonyl azide; triethylamine; In acetonitrile; for 3h; Ambient temperature;

DOI:10.1139/v84-497

upstream raw materials:

4-nitrobenzyl chloride

ethyl acetoacetate

acetoacetic acid methyl ester

Downstream raw materials:

4-nitrobenzyl 2-diazo-3-oxo-butanoate

p-Nitrobenzyl 3-aminocrotonate

4-nitrobenzyl 3-((tert-butyldimethylsilyl)oxy)-2-diazobut-3-enoate

p-nitrobenzyl 2-diazo-3-(trimethylsilyl)oxy-3-butenoate