| Identification | More | [Name]
Tetracyanoethylene | [CAS]
670-54-2 | [Synonyms]
Ethene tetracarbonitrile
ETHYLENETETRACARBONITRILE
PERCYANOETHYLENE
TCNE
TETRACYANOETHYLENE
(NC)2CC(CN)2
1,1,2,2-Ethylenetetracarbonitrile
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
Tetracyanoethyleneoffwhitextl
Tetrcyanoethylene
Tetracyanoethylene,98% | [EINECS(EC#)]
211-578-0 | [Molecular Formula]
C6N4 | [MDL Number]
MFCD00001850 | [Molecular Weight]
128.09 | [MOL File]
670-54-2.mol |
| Chemical Properties | Back Directory | [Definition]
The first member
of a class of compounds called cyanocarbons. | [Appearance]
white to beige-brown crystalline powder, crystals | [Melting point ]
197-199 °C(lit.) | [Boiling point ]
223 °C | [density ]
1,348 g/cm3 | [refractive index ]
1.5600 | [Fp ]
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]
670-54-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T+ | [Risk Statements ]
R20/21:Harmful by inhalation and in contact with skin .
R28:Very Toxic if swallowed.
R23/24:Toxic by inhalation and in contact with skin . | [Safety Statements ]
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S22:Do not breathe dust .
S1:Keep locked up . | [RIDADR ]
UN 2811 6.1/PG 1
| [WGK Germany ]
3
| [RTECS ]
KM7300000
| [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29269095 |
| Questions And Answer | Back Directory | [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.
|
| Hazard Information | Back Directory | [Chemical Properties]
white to beige-brown crystalline powder, crystals | [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]
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. | [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.] |
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