Triethyl 2-cyanopropane-1,2,3-tricarboxylate

Base Information

• Chemical Name: Triethyl 2-cyanopropane-1,2,3-tricarboxylate
• CAS No.: 20822-61-1
• Molecular Formula: C13H19NO6
• Molecular Weight: 285.297
• NSC Number: 99377
• DSSTox Substance ID: DTXSID40295039
• Wikidata: Q82034711
• Mol file: 20822-61-1.mol

Synonyms:triethyl 2-cyanopropane-1,2,3-tricarboxylate;20822-61-1;NSC99377;1,2,3-Propanetricarboxylic acid, 2-cyano-, 1,2,3-triethyl ester;NCIOpen2_006715;SCHEMBL14016347;DTXSID40295039;NSC-99377;beta-Cyanotricarballylic acid, triethyl ester;E79707;1,2,3-triethyl 2-cyanopropane-1,2,3-tricarboxylate

Chemical Property of Triethyl 2-cyanopropane-1,2,3-tricarboxylate

Chemical Property:

• Vapor Pressure: 1.22E-06mmHg at 25°C
• Boiling Point: 401°Cat760mmHg
• Flash Point: 175.4°C
• Density: 1.155g/cm³
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 285.12123733
• Heavy Atom Count: 20
• Complexity: 388

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Triethyl 2-cyanopropane-1,2,3-tricarboxylate

There total 2 articles about Triethyl 2-cyanopropane-1,2,3-tricarboxylate 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: 44.0%

sodium cyanide (773837-37-9) + chloroacetic acid ethyl ester (105-39-5) → diethyl 2-cyanosuccinate (10359-15-6) + triethyl 2-cyano-1,2,3-propanetricarboxylate (20822-61-1) + ethyl 2-cyanoacetate (105-56-6)

Guidance literature:

With tetrabutylammomium bromide; In dichloromethane; water; at 20 ℃; for 4h;

Reference yield: 20.0%

ethyl bromoacetate (105-36-2) + ethyl 2-cyanoacetate (105-56-6) → diethyl 2-cyanosuccinate (10359-15-6) + triethyl 2-cyano-1,2,3-propanetricarboxylate (20822-61-1)

Guidance literature:

With sodium ethanolate; In ethanol; at 0 - 23 ℃;

DOI:10.1021/co2001873

Reference yield:

triethyl 2-cyano-1,2,3-propanetricarboxylate (20822-61-1) → 2-Methyl-7-(phenylmethyl)-2,7-diazaspiro[4.4]-nonane-1,3,8-trione (91189-25-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / H₂, triethylamine / Raney cobalt / dimethylformamide / 23 h / 124116 - 279260 Torr

2: 76.2 percent / H₂O / 1.) RT, overnight, 2.) from RT to 220 deg C, 1 h

3: 1.) NaH / 1.) DMF, 1 h, 2.) RT, overnight

With hydrogen; sodium hydride; triethylamine; cobalt; In water; N,N-dimethyl-formamide;

DOI:10.1021/jm00170a035

upstream raw materials:

ethyl bromoacetate

ethyl 2-cyanoacetate

sodium cyanide

chloroacetic acid ethyl ester

Downstream raw materials:

(+/-)-3-Carboxy-5-oxo-3-pyrrolidineacetic acid

2-methyl-2,7-diazaspiro<4.4>nonane-1,3,8-trione

2-Methyl-7-(phenylmethyl)-2,7-diazaspiro[4.4]-nonane-1,3,8-trione

2-ethyl-7-(phenylmethyl)-2,7-diazaspiro[4.4]nonane-1,3,8-trione