Diethyl 3-oxohexanedioate

Base Information

• Chemical Name: Diethyl 3-oxohexanedioate
• CAS No.: 7149-59-9
• Molecular Formula: C10H16O5
• Molecular Weight: 216.234
• Hs Code.: 2918300090
• European Community (EC) Number: 230-479-3
• NSC Number: 72263
• DSSTox Substance ID: DTXSID40221712
• Nikkaji Number: J227.408F
• Wikidata: Q72462059
• Mol file: 7149-59-9.mol

Synonyms:Diethyl 3-oxohexanedioate;7149-59-9;3-Oxohexanedioic acid diethyl ester;Diethyl 3-oxoadipate;3-Oxo-hexanedioic acid diethyl ester;Hexanedioic acid, 3-oxo-, diethyl ester;EINECS 230-479-3;Diethyl3-oxohexanedioate;Diethyl-3-oxoadipate;diethyl beta-oxoadipate;Diethyl |?-ketoadipate;Diethyl beta-ketoadipate;Diethyl 3-oxohexanedioate #;1,6-diethyl 3-oxohexanedioate;SCHEMBL1224654;DTXSID40221712;beta-Ketoadipic acid diethyl ester;NSC72263;NSC 72263;NSC-72263;AKOS015843399;3-oxohexane-1,6-dioic acid diethyl ester;Hexanedioic acid,3-oxo-,1,6-diethyl ester;A9359;CS-0331260;FT-0636368

Chemical Property of Diethyl 3-oxohexanedioate

Chemical Property:

• Vapor Pressure: 0.00202mmHg at 25°C
• Refractive Index: 1.438
• Boiling Point: 290.8 °C at 760 mmHg
• PKA: 10.38±0.46(Predicted)
• Flash Point: 123.9 °C
• PSA: 69.67000
• Density: 1.093 g/cm³
• LogP: 0.85200
• Storage Temp.: −20°C
• Solubility.: Chloroform, Ethyl Acetate
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 216.09977361
• Heavy Atom Count: 15
• Complexity: 234

Purity/Quality:

99%, ^*data from raw suppliers

3-OxohexanedioicAcidDiethylEster ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)CCC(=O)CC(=O)OCC
• Uses: 3-Oxohexanedioic Acid Diethyl Ester is an intermediate used to prepare CMPF (C595000) which is a drug-binding inhibitor which is also a constituent of urine. CMPF can inhibit specific T4 binding in serum by increasing the free concentration of direct competitors.

Technology Process of Diethyl 3-oxohexanedioate

There total 29 articles about Diethyl 3-oxohexanedioate 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: 93.0%

ethanol (64-17-5) + ethyl (E)-5-oxotetrahydrofuran-2-ylideneacetate (57691-01-7) → diethyl 3-oxoadipate (7149-59-9)

Guidance literature:

With sodium ethanolate; for 2.5h; Ambient temperature;

Reference yield: 82.0%

butanedioic acid, monoethyl ester (1070-34-4) + ethyl potassium malonate (6148-64-7) → diethyl 3-oxoadipate (7149-59-9)

Guidance literature:

butanedioic acid, monoethyl ester; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 20 - 30 ℃; for 1h;

ethyl potassium malonate; With magnesium chloride; In tetrahydrofuran; at 60 ℃; for 1h;

Reference yield: 82.0%

3-Oxo-2-trimethylstannanylmethyl-pentanedioic acid diethyl ester → diethyl 3-oxoadipate (7149-59-9)

Guidance literature:

With niobium pentachloride; In dichloromethane; at -17 ℃; for 2h;

DOI:10.1039/CC9960002353

upstream raw materials:

2-acetyl-3-oxo-adipic acid diethyl ester

2-oxo-butane-1,1,4-tricarboxylic acid-1,1-diethyl ester

triethyl succinylmalonate

ethanol

Downstream raw materials:

2-(2-Bromo-propionyl)-3-oxo-hexanedioic acid diethyl ester

2-hydroxyimino-3-oxo-adipic acid-6-ethyl ester-1-benzyl ester

2-amino-3-oxo-adipic acid-1-benzyl ester

4-oxo-4-cyclopentylbutanoic acid

Refernces

• 1、 -. "PYRIMIDINE COMPOUNDS CONTAINING ACIDIC GROUPS". Paragraph 1170; 1171. . Retrieved 2018/06/15.
• 2、 -. "BENZOXAZEPINE COMPOUND". Page/Page column 26-27. . Retrieved 2010/11/08.