Methyl 3-(2-nitrophenyl)-2-oxopropanoate

Base Information

• Chemical Name: Methyl 3-(2-nitrophenyl)-2-oxopropanoate
• CAS No.: 79547-07-2
• Molecular Formula: C10H9 N O5
• Molecular Weight: 223.185
• European Community (EC) Number: 279-179-4
• DSSTox Substance ID: DTXSID201000584
• Nikkaji Number: J319.281D
• Wikidata: Q82994259
• Mol file: 79547-07-2.mol

Synonyms:methyl 3-(2-nitrophenyl)-2-oxopropanoate;79547-07-2;Methyl 3-(o-nitrophenyl)pyruvate;EINECS 279-179-4;SCHEMBL7633450;BJUFXOPELRQGNJ-UHFFFAOYSA-N;methyl 3-(2-nitrophenyl)pyruvate;DTXSID201000584;AKOS024385244;CS-0108628;Benzenepropanoic acid,2-nitro-a-oxo-,methyl ester;2-Nitro-alpha-oxobenzenepropanoic acid methyl ester

Chemical Property of Methyl 3-(2-nitrophenyl)-2-oxopropanoate

Chemical Property:

• Vapor Pressure: 3.54E-05mmHg at 25°C
• Boiling Point: 353.6°C at 760 mmHg
• Flash Point: 164.1°C
• PSA: 89.19000
• Density: 1.33g/cm³
• LogP: 1.40260
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 223.04807239
• Heavy Atom Count: 16
• Complexity: 296

Purity/Quality:

99% ^*data from raw suppliers

METHYL 3-(2-NITROPHENYL)-2-OXOPROPANOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(=O)CC1=CC=CC=C1[N+](=O)[O-]

Technology Process of Methyl 3-(2-nitrophenyl)-2-oxopropanoate

There total 6 articles about Methyl 3-(2-nitrophenyl)-2-oxopropanoate 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: 79.0%

methanol (67-56-1) + trans-5-(2-nitrobenzyliden)-2,2-dimethyl-1,3-oxazolidin-4-one → methyl 3-(2-nitrophenyl)-2-oxopropanoate (79547-07-2)

Guidance literature:

With hydrogenchloride; at 0 - 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2018.09.039

Reference yield: 61.0%

Dimethyl oxalate (553-90-2) + 1-methyl-2-nitrobenzene (88-72-2) → methyl 3-(2-nitrophenyl)-2-oxopropanoate (79547-07-2)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jm101007q

Reference yield:

2-nitro-benzaldehyde (552-89-6) → methyl 3-(2-nitrophenyl)-2-oxopropanoate (79547-07-2)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium ethanolate / ethanol / 5 h / 20 °C

2: hydrogenchloride / 24 h / 20 °C

3: potassium carbonate / methanol / 12 h / 20 °C

4: hydrogenchloride / 24 h / 0 - 20 °C

With hydrogenchloride; sodium ethanolate; potassium carbonate; In methanol; ethanol;

DOI:10.1016/j.tetlet.2018.09.039

upstream raw materials:

Dimethyl oxalate

1-methyl-2-nitrobenzene

methanol

2-nitro-benzaldehyde

Downstream raw materials:

indole-2-carboxylic acid methyl ester

2-Hydroxyimino-3-<2-nitro-phenyl>-propionsaeure-methylester

1-hydroxy-1H-indole-2-carboxylic acid

methyl 3-(2-nitrophenyl)-2-oxobut-3-enoate

Refernces

• 1、 Park, Yeon Kyeong,Lee, Sang Hyup. "Synthesis of New 1-Hydroxyindole-2-Carboxylates and Mechanistic Studies on Reaction Pathways". . p. 1995 - 2002. Retrieved 2017/05/29.
• 2、 Granchi, Carlotta,Roy, Sarabindu,Giacomelli, Chiara,MacChia, Marco,Tuccinardi, Tiziano,Martinelli, Adriano,Lanza, Mario,Betti, Laura,Giannaccini, Gino,Lucacchini, Antonio,Funel, Nicola,León, Leticia G.,Giovannetti, Elisa,Peters, Godefridus J.,Palchaudhuri, Rahul,Calvaresi, Emilia C.,Hergenrother, Paul J.,Minutolo, Filippo. "Discovery of N-hydroxyindole-based inhibitors of human lactate dehydrogenase isoform A (LDH-A) as starvation agents against cancer cells". supporting information; experimental part. p. 1599 - 1612. Retrieved 2011/06/21.