Diethyl 2-methyl-3-oxosuccinate

Base Information

• Chemical Name: Diethyl 2-methyl-3-oxosuccinate
• CAS No.: 759-65-9
• Molecular Formula: C9H14 O5
• Molecular Weight: 202.207
• Hs Code.: 2918300090
• European Community (EC) Number: 212-071-7
• NSC Number: 33946
• DSSTox Substance ID: DTXSID50883562
• Nikkaji Number: J26.314A
• Wikidata: Q27102127
• Metabolomics Workbench ID: 45414
• Mol file: 759-65-9.mol

Synonyms:Diethyl 2-methyl-3-oxosuccinate;759-65-9;Diethyl oxalpropionate;Methyloxalacetic Acid Diethyl Ester;diethyl 2-methyl-3-oxobutanedioate;Diethyl methyloxobutanedioate;Butanedioic acid, methyloxo-, diethyl ester;Diethyl Methyloxalacetate;Diethyl 3-methyl-2-oxosuccinate;Ethyl alpha-ethoxalylpropionate;Diethyl 2-methyloxosuccinate;Oxalacetic acid, methyl-, diethyl ester;Ethyl 2-Ethoxalylpropionate;Butanedioic acid, 2-methyl-3-oxo-, 1,4-diethyl ester;1,4-diethyl 2-methyl-3-oxobutanedioate;NSC 33946;Propanoic acid, 2-(ethoxyoxoacetyl)-, ethyl ester;Ethyl .alpha.-ethoxalylpropionate;EINECS 212-071-7;MFCD00009163;DIETHYL-2-METHYL-3-OXOSUCCINATE;AI3-05834;Butanedioic acid, 2-methyl-3-oxo-, diethyl ester;SCHEMBL60410;Diethyl2-methyl-3-oxosuccinate;Diethyl oxalpropionate, >=95%;CHEBI:16879;2-Oxalpropionic acid diethylester;DTXSID50883562;methyl oxalacetic acid diethyl ester;NSC33946;HYL 2-METHYL-3-OXOSUCCINATE;NSC-33946;s6012;STL183349;2-Ethoxalylpropionic Acid Ethyl Ester;AKOS024015152;DS-9920;Methyloxo-butanedioic acid diethyl ester;SY046328;HY-128720;CS-0012602;FT-0632899;M0381;C04067;EN300-126196;F19543;O-6000;Oxalacetic acid, methyl-, diethyl ester (8CI);Diethyl oxalpropionate, purum, >=95.0% (GC);Q27102127;1,4-Butanedioic acid, 3-methyl-2-oxo-, diethyl ester;Z1269118429

Chemical Property of Diethyl 2-methyl-3-oxosuccinate

Chemical Property:

• Vapor Pressure: 0.0223mmHg at 25°C
• Refractive Index: n20/D 1.432(lit.)
• Boiling Point: 138 °C23 mm Hg(lit.)
• PKA: 9.30±0.46(Predicted)
• Flash Point: >230 °F
• PSA: 69.67000
• Density: 1.073 g/mL at 25 °C(lit.)
• LogP: 0.31780
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Hexane (Slightly), Methanol (Slightly)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 202.08412354
• Heavy Atom Count: 14
• Complexity: 233

Purity/Quality:

99.9% ^*data from raw suppliers

DiethylOxalopropionate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 23-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C)C(=O)C(=O)OCC
• Uses: Reactant involved in:? ;Synthesis of anticancer and antiviral agents1? ;Oxidation by organohypervalent iodine reagent2? ;Synthesis of monomers for preparation of functional polyesters3? ;Synthesis of calpain inhibitors4? ;Preparation of human A2A receptor antagonists5? ;Structural studies of dihydropteroate synthase inhibitors6 Diethyl Oxalopropionate is a useful precursor in the synthesis of 2-Methylcitric Acid (M265080); a metabolite of Citric Acid (C521000) that can also be formed from condensation of propionoyl-CoA and oxaloacetic acid catalyzed by a citrate synthase enzyme. Reactant involved in:Synthesis of anticancer and antiviral agentsOxidation by organohypervalent iodine reagentSynthesis of monomers for preparation of functional polyestersSynthesis of calpain inhibitorsPreparation of human A2A receptor antagonistsStructural studies of dihydropteroate synthase inhibitors

Technology Process of Diethyl 2-methyl-3-oxosuccinate

There total 8 articles about Diethyl 2-methyl-3-oxosuccinate 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: 67.0%

Ethyl propionate (105-37-3,20741-13-3) + oxalic acid diethyl ester (95-92-1) → diethyl oxalpropionate (759-65-9)

Guidance literature:

With sodium ethanolate; In ethanol; at 20 ℃; Inert atmosphere;

DOI:10.1021/jm401382v

Reference yield:

1-cyano-but-2-ene-1,2,3-tricarboxylic acid triethyl ester + ozone (10028-15-6) + ethyl acetate (141-78-6) → 2-oxo-propionic acid ethyl ester (617-35-6) + diethyl oxalpropionate (759-65-9)

Guidance literature:

damit enthaelt geringe Mengen γ-Methyl-α-cyan-aconitsaeure-triaethylester gibt Methyloxalessigsaeure-diaethylester;

DOI:10.1039/jr9320001079

Reference yield:

methyl iodide (74-88-4) → diethyl oxalpropionate (759-65-9)

Guidance literature:

at 100 ℃;

upstream raw materials:

diethyl ether

potassium ethoxide

Ethyl propionate

oxalic acid diethyl ester

Downstream raw materials:

3-Phenyl-2.4-dioxo-5-(1-aethoxycarbonyl-aethyliden)-imidazolidin

2-Oxobutyric acid

2-hydroxy-3-methylbutanedioic acid diethyl ester

4-hydroxy-3-methylquinoline-2-carboxylic acid ethyl ester

Refernces

• 1、 -. "AZAINDOLE COMPOUNDS, SYNTHESIS THEREOF, AND METHODS OF USING THE SAME". Paragraph 0168; 0237; 0238. . Retrieved 2015/02/18.
• 2、 Emerson, David W.,Titus, Richard L.,Gonzalez, Rowena M.. "Evidence for Ketene Intermediates in the Reactions of 2-Oxobutanedioic Acid Diesters with Alcohols and Water". . p. 3572 - 3576. Retrieved 2007/10/02.