Tetracyanoethylene

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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

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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)

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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

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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.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: T8809
Product name: Tetracyanoethylene
Purity: 98%
Packaging: 5g
Price: $91.7
Updated: 2024/03/01

Sigma-Aldrich

Product number: T8809
Product name: Tetracyanoethylene
Purity: 98%
Packaging: 25g
Price: $326
Updated: 2024/03/01

TCI Chemical

Product number: T0077
Product name: Tetracyanoethylene
Purity: >98.0%(N)
Packaging: 5g
Price: $69
Updated: 2024/03/01

TCI Chemical

Product number: T0077
Product name: Tetracyanoethylene
Purity: >98.0%(N)
Packaging: 25g
Price: $220
Updated: 2024/03/01

Alfa Aesar

Product number: A13945
Product name: Tetracyanoethylene
Purity: 98%
Packaging: 1g
Price: $32.1
Updated: 2024/03/01

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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.

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

Henan Fengda Chemical Co., Ltd

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

Career Henan Chemical Co

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

670-54-2, TetracyanoethyleneRelated Search:

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

1,1,2,2-Tetracyanoethene

1,1,2,2-Tetracyanoethylene

delta(sup2,2’)-bimalononitrile

delta2,2'-Bimalononitrile

Ethene, tetracyano-

Ethylene, tetracyano-

Tetracyanoethene

Tetracyanoαthylen(ausderSchmelze)

Tetracyanoαthylen(ausLOsung)

Tetrakyanethylen

TetracyanoethyL

PERCYANOETHYLENE

TCNE

TETRACYANOETHYLENE

ETHYLENETETRACARBONITRILE

Ethene tetracarbonitrile

Tetracyanoethyleneoffwhitextl

Tetrcyanoethylene

Tetracyanoethylene,98%

eth-1-ene-1,1,2,2-tetracarbonitrile

Ethylenetetracarbonitrile, Percyanoethylene, TCNE

1,1,2,2-Ethenetetracarbonitrile

Tetracyanoethylene, 98% 10GR

Ethylenetetracarbonitrile TCNE

TETRACYANOETHYLENE FOR SYNTHESIS

Ethene-1,1,2,2-tetracarbonitrile

Tetracyanoethylene, 2,3-Dicyanobut-2-ene-1,4-dinitrile

(NC)2CC(CN)2

1,1,2,2-Ethylenetetracarbonitrile

Tetracyanoethylene (TCNE )

NSC 24833

Tetracyanoethylene (purified by sublimation)

Tetracyanoethylene &gt

670-54-2

C6N4

CN2CCCN2

Organic Building Blocks

Nitrogen Compounds

Cyanides/Nitriles

Oxidation

Others

Synthetic Reagents

Building Blocks

C6 to C7

Charge Transfer Complexes for Organic Metals

TCNQ Derivatives

Acceptors (Charge Transfer Complexes)

organic compound

Acceptors (Charge Transfer Complexes)

Charge Transfer Complexes for Organic Metals

Functional Materials

TCNQ Derivatives