Diethyl ethoxymethylenemalonate

Base Information

• Chemical Name: Diethyl ethoxymethylenemalonate
• CAS No.: 87-13-8
• Deprecated CAS: 69731-53-9
• Molecular Formula: C10H16O5
• Molecular Weight: 216.234
• Hs Code.: 2922.49 Oral rat LD50: 925 mg/kg
• European Community (EC) Number: 201-725-7
• NSC Number: 62117,9068
• UNII: 6KF8220SZ8
• DSSTox Substance ID: DTXSID5052591
• Nikkaji Number: J61.661C
• Wikidata: Q27265050
• Mol file: 87-13-8.mol

Synonyms:diethyl (ethoxymethylene)malonate;diethyl ethoxymethylenemalonate

Chemical Property of Diethyl ethoxymethylenemalonate

Chemical Property:

• Appearance/Colour: clear colourless to light yellow liquid
• Vapor Pressure: 0.00388mmHg at 25°C
• Melting Point: -33 °C
• Refractive Index: 1.462
• Boiling Point: 280 °C at 760 mmHg
• Flash Point: 107.6 °C
• PSA: 61.83000
• Density: 1.08 g/cm³
• LogP: 1.03300
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Water Solubility.: insoluble
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 216.09977361
• Heavy Atom Count: 15
• Complexity: 224

Purity/Quality:

99% ^*data from raw suppliers

DiethylEthoxymethylidenemalonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38-42/43
• Safety Statements: 26-36/37/39-27-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: CCOC=C(C(=O)OCC)C(=O)OCC
• Uses: Intermediate in the production of Flumequine Diethyl ethoxymethylenemalonate is used for synthesis of pyrido[3,2-e]pyrimido[1,2-c]pyrimidines. Initially, it was used to monitor lysine decarboxylase activity. It is useful in the determination of amino acids by precolumn derivatization by using reversed-phase high-performance liquid chromatography (HPLC). It plays an important role in the Gould-Jacobs reaction to prepare quinolines. For example, anile reacts with this reagent to give 4-hydroxyquinoline. It acts as an intermediate in the production of flumequine, which is a fluoroquinolone antibiotic.

Technology Process of Diethyl ethoxymethylenemalonate

There total 17 articles about Diethyl ethoxymethylenemalonate 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: 98.86%

orthoformic acid triethyl ester (122-51-0) + diethyl malonate (105-53-3) → diethyl 2-ethoxymethylenemalonate (87-13-8)

Guidance literature:

With 1,2-bis(N-methylimidazolium)ethanechloroaluminate; acetic anhydride; at 125 ℃; for 8h; Reagent/catalyst; Temperature;

Reference yield: 96.0%

ethanol (64-17-5) + diethyl 2-(chloromethylene)malonate (28783-51-9) → diethyl 2-ethoxymethylenemalonate (87-13-8)

Guidance literature:

With pyridine; for 0.25h; Ambient temperature;

DOI:10.1016/S0957-4166(97)00018-9

Reference yield: 95.2%

ethanol (64-17-5) + carbon monoxide (201230-82-2) + diethyl malonate (105-53-3) → diethyl 2-ethoxymethylenemalonate (87-13-8)

Guidance literature:

carbon monoxide; diethyl malonate; With dibenzo-24-crown ether; sodium ethanolate; In ethanol; at 100 ℃; for 2h; under 15001.5 Torr; Autoclave;

ethanol; With hydrogenchloride; In water; at 20 ℃; for 4h; Reagent/catalyst;

upstream raw materials:

acetic anhydride

(E)-3-Ureido-but-2-enoic acid ethyl ester

orthoformic acid triethyl ester

diethyl malonate

Downstream raw materials:

4-oxo-1,4-dihydro-[1,5]naphthyridin-3-yl carboxylic acid ethyl ester

2-(pyridin-3-yl)aminomethylene-malonic acid diethyl ester

6-ethoxycarbonyl-5-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine

diethyl <(pyrimidin-2-yl)aminomethylene>malonate

Refernces

• 1、 Jin, Guofan,Li, Zhenwang,Qi, Xueyong,Sun, Xianyu,Xiao, Fuyan,Zhao, Lei. "Design, Synthesis, and Dual Evaluation of Quinoline and Quinolinium Iodide Salt Derivatives as Potential Anticancer and Antibacterial Agents". . . Retrieved 2020/03/13.
• 2、 -. "Green pepper flavor compound, preparation method thereof, food additive and green pepper flavor food". Paragraph 0058; 0063-0065; 0076; 0081-0083; 0088; 0093-0095. . Retrieved 2020/07/21.