Tetracyanoethylene

Base Information

• Chemical Name: Tetracyanoethylene
• CAS No.: 670-54-2
• Deprecated CAS: 51778-96-2,56875-27-5
• Molecular Formula: C6N4
• Molecular Weight: 128.093
• Hs Code.: 29269095
• European Community (EC) Number: 211-578-0
• NSC Number: 24833
• UNII: C592309ECU
• DSSTox Substance ID: DTXSID7049425
• Nikkaji Number: J7.085H,J2.225.846J
• Wikipedia: Tetracyanoethylene
• Wikidata: Q413864
• ChEMBL ID: CHEMBL3188794
• Mol file: 670-54-2.mol

Synonyms:Ethenetetracarbonitrile(6CI,8CI,9CI); 1,1,2,2-Tetracyanoethene; 1,1,2,2-Tetracyanoethylene; Ethene,tetracyano-; Ethylenetetracarbonitrile; NSC 24833; TCNE; Tetracyanoethene;Tetracyanoethylene; D2,2'-Bimalononitrile

Chemical Property of Tetracyanoethylene

Chemical Property:

• Appearance/Colour: Beige powder.
• Vapor Pressure: 0.117mmHg at 25°C
• Melting Point: 197-199 ºC
• Refractive Index: 1.5600
• Boiling Point: 223 ºC
• Flash Point: 223ºC
• PSA: 95.16000
• Density: 1,348 g/cm³
• LogP: 0.37732
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: hydrolyzes
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 128.012296017
• Heavy Atom Count: 10
• Complexity: 289

Purity/Quality:

98% ^*data from raw suppliers

Tetracyanoethylene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T+
• Statements: 20/21-28-23/24
• Safety Statements: 28-36/37-45-28A-22-1

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C(#N)C(=C(C#N)C#N)C#N
• Description: Tetracyanoethylene (TCNE) is a crystalline solid with a melting point of 200 °C. DuPont researchers prepared it in 1957 by treating dibromomalononitrile with copper in boiling benzene. TCNE is an excellent electron acceptor and has been used to prepare organic superconductors. Tetracyanoethylene is a chemical compound of cyanide. It is used to prepare numerous organic superconductors, usually by serving as a single electron oxidant of an organic electron donor. Such charge-transfer salts are sometimes called Bechgaard salt.
• Uses: In the synthesis of spiro Compounds, in modified Diels-Alder reactions, as aromatizing agent: Longone, Smith, Tetrahedron Lett. 1962, 205. Used for postfunctional addition to polyphenylacetylene derivatives to change the oxygen permeability. As reactant for Regioselective [2+2] cycloaddition reaction for production of BODIPY dyes2 and TCBD derivatives, Thermal addition reaction with alkynes, One-pot reactions with nucleophilic reagents forming aromatic cyanovinyl compounds, Synthesis of cobalt tetracyanoethylene films, Biotransformation by Botrytis cinerea. Used for postfunctional addition to polyphenylacetylene derivatives to change the oxygen permeabilityReactant for: Regioselective [2+2] cycloaddition reaction for production of BODIPY dyes and TCBD derivativesThermal addition reaction with alkynesOne-pot reactions with nucleophilic reagents forming aromatic cyanovinyl compoundsSynthesis of cobalt tetracyanoethylene filmsBiotransformation by Botrytis cinerea

Technology Process of Tetracyanoethylene

There total 132 articles about Tetracyanoethylene 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: 100.0%

tetracyanoethylene potassium salt → ethenetetracarbonitrile (670-54-2)

Guidance literature:

With sulfur dichloride; In acetonitrile; at -40°C;

DOI:10.1021/ja00878a017

Reference yield: 37.0%

malononitrile (109-77-3) → ethenetetracarbonitrile (670-54-2)

Guidance literature:

With selenium(IV) oxide; In toluene; at 100 ℃; for 1.25h;

DOI:10.1134/S1070428017030253

Reference yield: 17.0%

disulfur dichloride (10025-67-9) + dibromomalononitrile (1885-23-0) → ethenetetracarbonitrile (670-54-2)

Guidance literature:

In 1,1,2,2-tetrachloroethylene; chloroform; refluxing of soln. of educts (8 h), distn. of solvent, warming of residue at 100-150°C and 20-40 Torr (2 h); sublimation, recrystn. (twice) from chlorobenzene;

DOI:10.1021/ja01544a051

upstream raw materials:

dibromomalononitrile

malononitrile

1,1,2,2,-tetracyanoethane

dimethylsulfonium dicyanomethylide

Downstream raw materials:

(4-chloro-anilino)-ethenetricarbonitrile

2,6-dimethyl-4-tricyanovinylaniline

2-Cyano-3-(2,6-dimethyl-phenylamino)-but-2-enedinitrile

3-Tricyanovinylindol

Refernces

• 1、 Haga, Naoki,Nakajima, Hiroyuki,Takayanagi, Hiroaki,Tokumaru, Katsumi. "Photoinduced Electron Transfer between Acenaphthylene and Tetracyanoethylene: Effect of Irradiation Mode on Reactivity of the Charge-Transfer Complex and the Resulted Radical Ion Pair in Solution and Crystalline State". . p. 5372 - 5384. Retrieved 1998.
• 2、 Kachanov,Slabko, O. Yu.,Kaminskii. "Synthesis of tetracyanoethylene by oxidative dimerization of malononitrile". . p. 462 - 464. Retrieved 2017.
• 3、 Madrahimov, Sherzod,Mostafa, Adel,Yempally, Veeranna,Fadlallah, Joelle,AlQaradawi, Siham Y.. "Electronic, infrared, mass spectrometry and thermal studies on the reaction of 2-amino-6-methylpyridine with π-acceptors". . . Retrieved 2019/09/10.
• 4、 El-Habeeb, Abeer A.,Al-Saif, Foziah A.,Refat, Moamen S.. "Spectroscopic and thermal investigations on the charge transfer interaction between risperidone as a schizophrenia drug with some traditional π-acceptors: Part 2". . p. 464 - 477. Retrieved 2013/04/23.