Diethyl 1,3-acetonedicarboxylate

Base Information

• Chemical Name: Diethyl 1,3-acetonedicarboxylate
• CAS No.: 105-50-0
• Deprecated CAS: 31096-04-5
• Molecular Formula: C9H14O5
• Molecular Weight: 202.207
• Hs Code.: 29183000
• European Community (EC) Number: 203-302-2
• NSC Number: 9013
• UNII: Q0CC9NL00V
• DSSTox Substance ID: DTXSID1059317
• Nikkaji Number: J134.662H
• Wikidata: Q72469039
• Mol file: 105-50-0.mol

Synonyms:Glutaricacid, 3-oxo-, diethyl ester (6CI,7CI,8CI);Glutaric acid, b-oxo-, diethyl ester (4CI);Pentanedioic acid, 3-oxo-, diethylester (9CI);3-Oxopentanedioic acid diethyl ester;Acetonedicarboxylic aciddiethyl ester;Diethyl2-oxopropane-1,3-dicarboxylate;Diethyl 3-ketoglutarate;Diethyl3-oxoglutarate;Diethyl 3-oxopentanedioate;Diethyl acetonedicarboxylate;Diethyl b-ketoglutarate;Diethyl b-oxoglutarate;NSC 9013;b-Ketoglutaric acid diethyl ester;Diethyl acetone-1,3-dicarboxylate;

Chemical Property of Diethyl 1,3-acetonedicarboxylate

Chemical Property:

• Appearance/Colour: clear colorless to pale yellow liquid
• Vapor Pressure: 0.0605mmHg at 25°C
• Melting Point: 125 °C
• Refractive Index: n20/D 1.440(lit.)
• Boiling Point: 250 °C at 760 mmHg
• PKA: 9.66±0.46(Predicted)
• Flash Point: 86.1 °C
• PSA: 69.67000
• Density: 1.116 g/cm³
• LogP: 0.46190
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: 10 g/L (20 ºC)
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 202.08412354
• Heavy Atom Count: 14
• Complexity: 199

Purity/Quality:

99% ^*data from raw suppliers

Diethyl3-Oxopentanedioate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CCOC(=O)CC(=O)CC(=O)OCC
• Uses: Diethyl 1,3-acetonedicarboxylate was used in the synthesis of novel pyrido[4,3,2-de]quinoline, isoquinolino[6,5,4,3-cde] quinoline and pyrazomycin. It was used as starting reagent in the synthesis of (±)-thienamycin, potent β-lactam antibiotic.

Technology Process of Diethyl 1,3-acetonedicarboxylate

There total 21 articles about Diethyl 1,3-acetonedicarboxylate 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: 53.0%

ethanol (64-17-5) + citric acid (77-92-9,906507-37-7) → diethyl 1,3-acetonedicarboxylate (105-50-0)

Guidance literature:

citric acid; With chlorosulfonic acid; In dichloromethane; at 10 ℃; for 5h;

ethanol; In dichloromethane; at 0 - 40 ℃; for 2h;

DOI:10.1021/acs.joc.8b02218

Reference yield:

acetonedicarboxylic acid (542-05-2) + ethanol (64-17-5) → diethyl 1,3-acetonedicarboxylate (105-50-0)

Guidance literature:

With hydrogenchloride;

Reference yield:

acetonedicarboxylic acid (542-05-2) → diethyl 1,3-acetonedicarboxylate (105-50-0)

Guidance literature:

With hydrogenchloride;

upstream raw materials:

acetonedicarboxylic acid

ethanol

diethyl α-acetylacetonedicarboxylate

2-oxo-propane-1,1,3-tricarboxylic acid triethyl ester

Downstream raw materials:

2-(4-nitro-benzyl)-3-(4-nitro-phenyl)-propionic acid

1-allyl-4-oxo-2,6-diphenyl-piperidine-3,5-dicarboxylic acid diethyl ester

4-Oxo-2,6-diphenyl-1-oxa-cyclohexane-3,5-ethyl dicarboxylate

3-oxo-glutaric acid di-p-toluidide

Refernces

Hydrogen Bonding and Bond Order in Phenylhydrazones: Structures of Diethyl 2-(o-Methylphenylhydrazono)-3-oxopentanedioate (1) and Two Forms of Diethyl 2-(p-Nitrophenylhydrazono)-3-oxopentanedioate

10.1107/S0567740882006281

The research aimed to investigate the hydrogen bonding and bond order in phenylhydrazones, specifically focusing on the structures of diethyl 2-(o-methylphenylhydrazono)-3-oxopentanedioate (1) and two forms of diethyl 2-(p-nitrophenylhydrazono)-3-oxopentanedioate (2a and 2b). The study used infrared (IR) and proton nuclear magnetic resonance (1H NMR) spectroscopy to analyze intramolecular hydrogen bonding between the ester carbonyl and the hydrazone hydrogen in these compounds. The crystal structures of the molecules were determined, confirming the presence of intramolecular hydrogen bonding between the ester carbonyl and the hydrogen on N(7) of the hydrazone group. The research concluded that the ester carbonyl group, rather than the keto-carbonyl group, participates in intramolecular hydrogen bonding, and provided further insights into bond-geometry relationships in phenylhydrazones. The chemicals used in the process included diethyl 3-oxopentanedioate, substituted benzenediazonium salts, p-nitroaniline, sodium nitrite, and other reagents for the synthesis and crystallization of the compounds under study.