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Tetracyanoethylene

Description

Tetracyanoethylene

CAS No.670-54-2
Chemical Name:Tetracyanoethylene
CBNumber:CB9854093
Molecular Formula:C6N4
Formula Weight:128.09
MOL File:670-54-2.mol

Tetracyanoethylene Property

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)
FDA UNII C592309ECU
NIST Chemistry Reference Tetracyanoethylene(670-54-2)
EPA Substance Registry System Ethenetetracarbonitrile (670-54-2)
UNSPSC Code 12352117
NACRES NA.22

Safety

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

NFPA 704:

	0
4		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H300-H312+H332
Precautionary statements P261-P264-P280-P301+P310-P302+P352+P312-P304+P340+P312

Tetracyanoethylene Price More Price(10)

Brand: Sigma-Aldrich(India)
Product number: T8809
Product name : Tetracyanoethylene
Purity: 96%
Packaging: 5G
Price: ₹5401.68
Updated: 2022/06/14
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Brand: Sigma-Aldrich(India)
Product number: T8809
Product name : Tetracyanoethylene
Purity: 96%
Packaging: 25G
Price: ₹24107.28
Updated: 2022/06/14
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Brand: TCI Chemicals (India)
Product number: T3264
Product name : Tetracyanoethylene (purified by sublimation)
Purity:
Packaging: 1G
Price: ₹2700
Updated: 2022/05/26
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Brand: TCI Chemicals (India)
Product number: T3264
Product name : Tetracyanoethylene (purified by sublimation)
Purity:
Packaging: 5G
Price: ₹9000
Updated: 2022/05/26
Buy: Buy

Brand: TCI Chemicals (India)
Product number: T0077
Product name : Tetracyanoethylene
Purity:
Packaging: 5G
Price: ₹5800
Updated: 2022/05/26
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Tetracyanoethylene Chemical Properties,Usage,Production

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

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.
reaction suitability reagent type: oxidant
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.]