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;PERCYANOETHYLENE;Tetrakyanethylen;Tetrcyanoethylene;TETRACYANOETHYLENE
- CBNumber:
- CB9854093
- Molecular Formula:
- C6N4
Lewis structure
- Molecular Weight:
- 128.09
- MDL Number:
- MFCD00001850
- MOL File:
- 670-54-2.mol
| 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) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS06 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H300-H312+H332 | |||||||||
| Precautionary statements | P261-P264-P280-P301+P310-P302+P352+P312-P304+P340+P312 | |||||||||
| 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 |
|
Tetracyanoethylene price More Price(23)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | T8809 | Tetracyanoethylene 98% | 670-54-2 | 5g | $91.7 | 2024-03-01 | Buy |
| Sigma-Aldrich | T8809 | Tetracyanoethylene 98% | 670-54-2 | 25g | $326 | 2024-03-01 | Buy |
| TCI Chemical | T0077 | Tetracyanoethylene >98.0%(N) | 670-54-2 | 5g | $69 | 2024-03-01 | Buy |
| TCI Chemical | T0077 | Tetracyanoethylene >98.0%(N) | 670-54-2 | 25g | $220 | 2024-03-01 | Buy |
| Alfa Aesar | A13945 | Tetracyanoethylene 98% | 670-54-2 | 1g | $32.1 | 2024-03-01 | Buy |
Tetracyanoethylene Chemical Properties,Uses,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
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.
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
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Henan Fengda Chemical Co., Ltd | +86-371-86557731 +86-13613820652 | info@fdachem.com | China | 7613 | 58 |
| Hangzhou FandaChem Co.,Ltd. | 008657128800458; +8615858145714 | fandachem@gmail.com | China | 9348 | 55 |
| career henan chemical co | +86-0371-86658258 | sales@coreychem.com | China | 29914 | 58 |
| Hubei xin bonus chemical co. LTD | 86-13657291602 | linda@hubeijusheng.com | CHINA | 22968 | 58 |
| Chongqing Chemdad Co., Ltd | +86-023-61398051 +8613650506873 | sales@chemdad.com | China | 39916 | 58 |
| CONIER CHEM AND PHARMA LIMITED | +8618523575427 | sales@conier.com | China | 47465 | 58 |
| Dayang Chem (Hangzhou) Co.,Ltd. | 571-88938639 +8617705817739 | info@dycnchem.com | CHINA | 52867 | 58 |
| changzhou huayang technology co., ltd | +8615250961469 | 2571773637@qq.com | China | 9821 | 58 |
| Shaanxi Didu New Materials Co. Ltd | +86-89586680 +86-13289823923 | 1026@dideu.com | China | 9165 | 58 |
| LEAP CHEM CO., LTD. | +86-852-30606658 | market18@leapchem.com | China | 24738 | 58 |
View Lastest Price from Tetracyanoethylene manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
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2023-12-23 | Tetracyanoethylene
670-54-2
|
US $50.00-1.00 / KG | 1KG | 99% | g-kg-tons, free sample is available | Henan Fengda Chemical Co., Ltd | |
 |
2022-09-03 | Tetracyanoethylene
670-54-2
|
US $0.00 / KG | 25KG | 97% | 1tons | Henan Aochuang Chemical Co.,Ltd. | |
 |
2019-07-06 | Tetracyanoethylene (TCNE )
670-54-2
|
US $1850.00-1750.00 / KG | 5KG | 98% by Kjedahl | 400kg per month | Career Henan Chemical Co |
-
- Tetracyanoethylene
670-54-2
- US $50.00-1.00 / KG
- 99%
- Henan Fengda Chemical Co., Ltd
-
- Tetracyanoethylene
670-54-2
- US $0.00 / KG
- 97%
- Henan Aochuang Chemical Co.,Ltd.
-
- Tetracyanoethylene (TCNE )
670-54-2
- US $1850.00-1750.00 / KG
- 98% by Kjedahl
- Career Henan Chemical Co
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