Diethyl 2,3-dicyanofumarate

Base Information

• Chemical Name: Diethyl 2,3-dicyanofumarate
• CAS No.: 35234-88-9
• Molecular Formula: C10H10 N2 O4
• Molecular Weight: 222.2
• Hs Code.: 2926909090
• European Community (EC) Number: 252-453-0
• UNII: B9V4T4GNN6
• DSSTox Substance ID: DTXSID301262232
• Nikkaji Number: J289.944B
• Wikidata: Q76303653
• Mol file: 35234-88-9.mol

Synonyms:Diethyl 2,3-dicyanofumarate;DIETHYL DICYANOFUMARATE;35234-88-9;DIETHYL DICYANOFUMARATE, 97;EINECS 252-453-0;1,4-Diethyl (2E)-2,3-dicyano-2-butenedioate;diethyl (E)-2,3-dicyanobut-2-enedioate;B9V4T4GNN6;diethyl (2E)-2,3-dicyanobut-2-ene-1,4-dioate;SCHEMBL1754710;DTXSID301262232;2,3-Dicyanofumaric acid diethyl ester;AKOS001025555;1,4-Diethyl 2,3-dicyano-2-butenedioate;1,4-DIETHYL (2E)-2,3-DICYANOBUT-2-ENEDIOATE;2-Butenedioic acid, 2,3-dicyano-, 1,4-diethyl ester;2-Butenedioic acid, 2,3-dicyano-, 1,4-diethyl ester, (2E)-;InChI=1/C10H10N2O4/c1-3-15-9(13)7(5-11)8(6-12)10(14)16-4-2/h3-4H2,1-2H3/b8-7

Chemical Property of Diethyl 2,3-dicyanofumarate

Chemical Property:

• Vapor Pressure: 0.000106mmHg at 25°C
• Melting Point: 114-118 °C(lit.)
• Boiling Point: 337.3°Cat760mmHg
• Flash Point: 147.1°C
• PSA: 100.18000
• Density: 1.23g/cm³
• LogP: 0.45636
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 222.06405680
• Heavy Atom Count: 16
• Complexity: 379

Purity/Quality:

98%Min ^*data from raw suppliers

Diethyldicyanofumarate 96% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 26-27-36-36/39

MSDS Files:

Useful:

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

Technology Process of Diethyl 2,3-dicyanofumarate

There total 12 articles about Diethyl 2,3-dicyanofumarate 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: 94.0%

ethyl 2-cyanoacetate (105-56-6) → diethyl dicyanofumarate (35234-88-9)

Guidance literature:

With aluminum oxide; potassium fluoride; iodine; In acetonitrile; for 16h; Ambient temperature; Irradiation;

DOI:10.1080/00397919208021130

Reference yield: 75.0%

cyanogen iodide (506-78-5) + acetylenedicarboxylic acid diethyl ester (762-21-0) → diethyl dicyanofumarate (35234-88-9)

Guidance literature:

With copper diacetate; In toluene; at 80 ℃; for 20h; Inert atmosphere;

DOI:10.1021/acs.orglett.7b01378

Reference yield: 10.0%

ethyl cyano<thio>acetate (81852-22-4) → diethyl dicyanofumarate (35234-88-9) + N,N-dimethyl-N'-phenylthiourea (705-62-4)

Guidance literature:

With triethylamine; In dichloromethane; for 50h;

upstream raw materials:

ethyl 2-cyanoacetate

ethyl bromocyanoacetate

ethyl cyano<thio>acetate

selenium(IV) oxide

Downstream raw materials:

2,3-Dicyano-2-(4,4-dimethyl-2,6-dioxo-cyclohexyl)-succinic acid diethyl ester

N-<4-Methoxy-phenyl>-trans-α.β-dicyano-β-ethoxycarbonyl-vinylamin

N-<4-Methoxy-phenyl>-trans-α.β-diethoxycarbonyl-β-cyano-vinylamin

4-(α.β-Dicyano-α.β-diethoxycarbonyl-ethyl)-N.N-dimethyl-anilin

Refernces

• 1、 Sakata, Naoki,Sasakura, Kohei,Matsushita, Gaku,Okamoto, Kazuhiro,Ohe, Kouichi. "Copper-Catalyzed Regio- and Stereoselective Iodocyanation and Dicyanation of Alkynes with Cyanogen Iodide". supporting information. p. 3422 - 3425. Retrieved 2017/07/15.
• 2、 Carling, Carl-Johan,Boyer, John-Christopher,Branda, Neil R.. "Remote-control photoswitching using NIR light". supporting information; body text. p. 10838 - 10839. Retrieved 2009/12/04.