Diethyl(2-cyanoethyl)(methyl)propanedioate

Base Information

• Chemical Name: Diethyl(2-cyanoethyl)(methyl)propanedioate
• CAS No.: 10444-11-8
• Molecular Formula: C₁₁H₁₇NO₄
• Molecular Weight: 227.26
• NSC Number: 157557
• DSSTox Substance ID: DTXSID70303257
• Wikidata: Q82048441
• Mol file: 10444-11-8.mol

Synonyms:10444-11-8;diethyl(2-cyanoethyl)(methyl)propanedioate;NSC157557;DTXSID70303257;NSC-157557

Chemical Property of Diethyl(2-cyanoethyl)(methyl)propanedioate

Chemical Property:

• Vapor Pressure: 0.000145mmHg at 25°C
• Boiling Point: 332.5°Cat760mmHg
• Flash Point: 144.9°C
• Density: 1.079g/cm³
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 227.11575802
• Heavy Atom Count: 16
• Complexity: 284

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C)(CCC#N)C(=O)OCC

Technology Process of Diethyl(2-cyanoethyl)(methyl)propanedioate

There total 4 articles about Diethyl(2-cyanoethyl)(methyl)propanedioate 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: 85.9%

carbon monoxide (201230-82-2) + acrylonitrile (107-13-1,25014-41-9) + Diethyl methylmalonate (609-08-5) → 4-cyano-2-(ethoxycarbonyl)-2-methylbutanoic acid ethyl ester (10444-11-8)

Guidance literature:

With pyridine; dicobalt octacarbonyl; In 1,4-dioxane; at 75 ℃; for 3h; under 750.06 Torr;

DOI:10.1021/jo00295a049

Reference yield:

acrylonitrile (107-13-1,25014-41-9) + Diethyl methylmalonate (609-08-5) → 4-cyano-2-(ethoxycarbonyl)-2-methylbutanoic acid ethyl ester (10444-11-8)

Guidance literature:

With potassium hydroxide; tert-butyl alcohol;

DOI:10.1039/jr9500001683

Reference yield:

dichloromethane (75-09-2) + diethyl 2-(2-cyanoethyl)malonate (17216-62-5) → 4-cyano-2-(ethoxycarbonyl)-2-methylbutanoic acid ethyl ester (10444-11-8) + 2-Chloromethyl-2-(2-cyano-ethyl)-malonic acid diethyl ester (122259-89-6)

Guidance literature:

With tetrabutylammomium bromide; In dichloromethane; at 20 ℃; Yield given. Yields of byproduct given; diaphragm cell, platinum cathode;

DOI:10.1007/BF00957199

upstream raw materials:

acrylonitrile

Diethyl methylmalonate

diethyl 2-(2-cyanoethyl)malonate

dimethyl sulfate

Downstream raw materials:

3-methyl-2-oxopiperidine-3-carboxylic acid ethyl ester