2,3-Dicyanomaleic acid dimethyl ester

Base Information

• Chemical Name: 2,3-Dicyanomaleic acid dimethyl ester
• CAS No.: 35234-87-8
• Molecular Formula: C8H6N2O4
• Molecular Weight: 194.147
• NSC Number: 167517
• Nikkaji Number: J663.667E
• Mol file: 35234-87-8.mol

Synonyms:NSC167517;35234-87-8;2,3-Dicyanomaleic acid dimethyl ester;NSC-167517

Chemical Property of 2,3-Dicyanomaleic acid dimethyl ester

Chemical Property:

• Vapor Pressure: 0.0006mmHg at 25°C
• Boiling Point: 310.4°C at 760 mmHg
• Flash Point: 134.7°C
• Density: 1.315g/cm³
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 194.03275668
• Heavy Atom Count: 14
• Complexity: 352

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(=C(C#N)C(=O)OC)C#N
• Isomeric SMILES: COC(=O)/C(=C(/C#N)\C(=O)OC)/C#N

Technology Process of 2,3-Dicyanomaleic acid dimethyl ester

There total 13 articles about 2,3-Dicyanomaleic acid dimethyl ester 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: 97.0%

cis,trans-1,4-bis(dimethylamino)buta-1,3-diene (74894-01-2) + dimethyl 2,3-dicyanomaleate (101342-44-3) → (E,E)-1,4-Bis(dimethylamino)-1,3-butadiene (123931-19-1) + dimethyl 2,3-dicyanofumarate (35234-87-8) + (1S,2S,3S,6R)-1,2-Dicyano-3,6-bis-dimethylamino-cyclohex-4-ene-1,2-dicarboxylic acid dimethyl ester (123858-33-3,123881-39-0)

Guidance literature:

In dichloromethane; at -50 ℃; for 0.0833333h;

Reference yield: 56.0%

(E)-2,3-Bis-(hydroxyimino-methyl)-but-2-enedioic acid dimethyl ester (115668-28-5) → dimethyl 2,3-dicyanofumarate (35234-87-8)

Guidance literature:

With pyridine; trifluoroacetic anhydride; In 1,4-dioxane; at 20 ℃;

DOI:10.1016/S0040-4020(97)00831-4

Reference yield: 46.0%

cyanoacetic acid 2-(2-cyanoacetoxy) ethyl ester (89976-96-5) + methyl 2-cyanoacetate (105-34-0) → dimethyl 2,3-dicyanofumarate (35234-87-8) + 2,3-dicyanobut-2-enedioic acid 2-(2,3-dicyano-3-methoxycarbonylacryloyloxy)ethyl ester methyl ester

Guidance literature:

With thionyl chloride; In tetrahydrofuran; for 16h; Reflux; Inert atmosphere;

DOI:10.1002/chem.200802145

upstream raw materials:

methyl 2-cyanoacetate

cis,trans-1,4-bis(dimethylamino)buta-1,3-diene

dimethyl 2,3-dicyanomaleate

methyl 2-bromo-2-cyanoacetate

Downstream raw materials:

4-Cyano-1H-pyrazole-3-carboxylic acid methyl ester

4-Cyan-1-methyl-3-pyrazolcarbonsaeure-methylester

4-Cyan-1-methyl-5-pyrazolcarbonsaeure-methylester

methyl 1-methyl-1H-1,2,3-triazole-5-carboxylate