Tetracyanoethylene
Description- Product Name
- Tetracyanoethylene
- CAS No.
- 670-54-2
- Chemical Name
- Tetracyanoethylene
- Synonyms
- TCNE;Ethene-1,1,2,2-tetracarbonitrile;NSC 24833;(NC)2CC(CN)2;TetracyanoethyL;Tetracyanoethene;Tetrakyanethylen;PERCYANOETHYLENE;Tetrcyanoethylene;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)
- NIST Chemistry Reference
- Tetracyanoethylene(670-54-2)
- EPA Substance Registry System
- Ethenetetracarbonitrile (670-54-2)
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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H300Fatal if swallowed
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
N-Bromosuccinimide Price
- Product number
- T8809
- Product name
- Tetracyanoethylene
- Purity
- 98%
- Packaging
- 5g
- Price
- $91.7
- Updated
- 2024/03/01
- Product number
- T8809
- Product name
- Tetracyanoethylene
- Purity
- 98%
- Packaging
- 25g
- Price
- $326
- Updated
- 2024/03/01
- Product number
- T0077
- Product name
- Tetracyanoethylene
- Purity
- >98.0%(N)
- Packaging
- 5g
- Price
- $69
- Updated
- 2024/03/01
- Product number
- T0077
- Product name
- Tetracyanoethylene
- Purity
- >98.0%(N)
- Packaging
- 25g
- Price
- $220
- Updated
- 2024/03/01
- Product number
- A13945
- Product name
- Tetracyanoethylene
- Purity
- 98%
- Packaging
- 1g
- Price
- $32.1
- Updated
- 2024/03/01
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. 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 Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from Tetracyanoethylene manufacturers
- Product
- Tetracyanoethylene 670-54-2
- Price
- US $50.00-1.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2023-12-22
- Product
- Tetracyanoethylene (TCNE ) 670-54-2
- Price
- US $1850.00-1750.00/KG
- Min. Order
- 5KG
- Purity
- 98% by Kjedahl
- Supply Ability
- 400kg per month
- Release date
- 2018-07-23