Diethyl cyanopropanedioate

Base Information

• Chemical Name: Diethyl cyanopropanedioate
• CAS No.: 4513-67-1
• Molecular Formula: C8H11 N O4
• Molecular Weight: 185.18
• NSC Number: 128082
• DSSTox Substance ID: DTXSID70299085
• Nikkaji Number: J1.841.652B
• Wikidata: Q82041275
• Mol file: 4513-67-1.mol

Synonyms:diethyl 2-cyanopropanedioate;diethyl cyanopropanedioate;4513-67-1;Propanedioic acid,2-cyano-, 1,3-diethyl ester;NSC128082;Cyanmalonsaurediathylester;SCHEMBL9705616;DTXSID70299085;PUFPZFYANODLJO-UHFFFAOYSA-N;2-cyanopropanedioic acid diethyl ester;NSC-128082;A826987

Chemical Property of Diethyl cyanopropanedioate

Chemical Property:

• Vapor Pressure: 0.00648mmHg at 25°C
• Boiling Point: 271.4°C at 760 mmHg
• Flash Point: 116.1°C
• Density: 1.147g/cm³
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 185.06880783
• Heavy Atom Count: 13
• Complexity: 222

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Diethyl cyanopropanedioate

There total 6 articles about Diethyl cyanopropanedioate 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%

diethyl 2-ethoxymethylenemalonate (87-13-8) → diethyl 2-cyanomalonate (4513-67-1) + diethyl N-ethoxyaminomethylenemalonate (145325-85-5) + ethyl 1-ethoxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylate (145325-80-0) + ethyl 5-ethoxyisoxazole-4-carboxylate (28783-55-3)

Guidance literature:

With sodium azide; trifluoroacetic acid; at 20 ℃; for 12h; Further byproducts given;

DOI:10.1071/CH9921571

Reference yield: 67.0%

diethyl 2-ethoxymethylenemalonate (87-13-8) → diethyl 2-cyanomalonate (4513-67-1) + diethyl N-ethoxyiminomethylmalonate (145325-83-3,145325-86-6) + ethyl 1-ethoxy-3-oxo-2,3-dihydro-1H-pyrazole-4-carboxylate (145325-80-0) + ethyl 5-ethoxyisoxazole-4-carboxylate (28783-55-3)

Guidance literature:

With sodium azide; trifluoroacetic acid; at 20 ℃; for 12h; Yield given. Further byproducts given. Title compound not separated from byproducts;

DOI:10.1071/CH9921571

Reference yield:

diethyl ether (60-29-7,927820-24-4) + bromocyane (506-68-3) + sodium diethylmalonate (996-82-7) → diethyl 2-cyanomalonate (4513-67-1) + 1,1,2,2-tetracarboethoxy-ethylene (6174-95-4) + tetraethyl ethane-1,1,2,2-tetracarboxylate (632-56-4) + sodium cyanide (143-33-9,25596-52-5)

Guidance literature:

upstream raw materials:

diethyl ether

bromocyane

sodium diethylmalonate

ethanol

Downstream raw materials:

Diethyl ketomalonate

malonic acid

carbon dioxide

ammonia

Refernces