Tetracyanoethylene Chemical Properties

Melting point:

197-199 °C(lit.)

Boiling point:

223 °C

Density 

1,348 g/cm³

refractive index 

1.5600

Flash point:

223°C

storage temp. 

2-8°C

form 

Crystalline Powder, Crystals or Chunks

color 

White to beige-brown

Water Solubility 

hydrolyzes

Sensitive 

Moisture Sensitive

λmax

328nm(CHCl3)(lit.)

Merck 

14,9195

BRN 

1679885

CAS DataBase Reference

670-54-2(CAS DataBase Reference)

NIST Chemistry Reference

Tetracyanoethylene(670-54-2)

EPA Substance Registry System

Ethenetetracarbonitrile (670-54-2)

Safety Information

Hazard Codes 

T+

Risk Statements 

20/21-28-23/24

Safety Statements 

28-36/37-45-28A-22-1

RIDADR 

UN 2811 6.1/PG 1

WGK Germany 

3

RTECS 

KM7300000

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

II

HS Code 

29269095

MSDS

• Language:English Provider:Ethylenetetracarbonitrile
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Tetracyanoethylene Usage And Synthesis

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.

Chemical Properties

white to beige-brown crystalline powder, crystals. Tetracyanoethylene [670-54-2], ethenetetracarbonitrile, TCNE, ( NC)2C = C (CN)2, Mr 128.09, mp 197 – 198℃, bp 223℃, n25 D 1.560. The preferred synthetic preparation of TCNE involves the debromination of the KBr complex of dibromomalononitrile. Tetracyanoethylene is a reactive compound that undergoes a variety of reactions including addition, replacement and cyclization. The chemistry of TCNE is exhaustively reviewed in.

Uses

In the synthesis of spiro Compounds, in modified Diels-Alder reactions, as aromatizing agent: Longone, Smith, Tetrahedron Lett. 1962, 205.

Uses

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.

Uses

Used for postfunctional addition to polyphenylacetylene derivatives to change the oxygen permeability

Reactant for:

• Regioselective [2+2] cycloaddition reaction for production of BODIPY dyes 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

Definition

The first member of a class of compounds called cyanocarbons.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 4, p. 877, 1963
The Journal of Organic Chemistry, 45, p. 5113, 1980 DOI: 10.1021/jo01313a019

Hazard

Hydrolyzes in moist air to hydrogen cyanide.

Purification Methods

Crystallise it from chlorobenzene, dichloroethane, or dichloromethane [Hall et al. J Org Chem 52 5528 1987]. Storeitat0oina desiccator over NaOH pellets. (It slowly evolves HCN on exposure to moist air CARE.) It can also be sublimed at 120o under vacuum. Also purify it by repeated sublimation at 120-130o/0.5mm. [Frey et al. J Am Chem Soc 107 748 1985, Traylor & Miksztal J Am Chem Soc 109 2778 1987, Fatiadi Synthesis 249 1986, Synthesis 749 1967, Beilstein 2 IV 1245.]

Tetracyanoethylene(670-54-2)Related Product Information

• Ethyl N-cyanoethanimideate
• Acrylonitrile
• ETHYL 2-CYANOACRYLATE
• Triethylenetetramine
• Sodium cyanoborohydride
• Methylene dithiocyanate
• 2-Chloro-3-cyanopyridine
• 1,4,7,10,13-Pentaazatridecane
• Tetrachloroethylene
• ETHYLENE
• Cyanoacetic acid
• Tetrahydropyran-4-carbaldehyde
• TRI-TERT-BUTYLPHOSPHONIUM TETRAPHENYLBORATE
• 3,4-Dithia-7H-cyclopenta[a]pentalene
• Menatetrenone
• Diphosphoryl chloride
• TERT-BUTYL TETRAHYDROPYRIMIDINE-1(2H)-CARBOXYLATE
• Tetrahydrofurfuryl alcohol