T8809
Tetracyanoethylene
96%
Synonym(s):
Ethylenetetracarbonitrile, NSC 24833, Percyanoethylene, TCNE
Sign Into View Organizational & Contract Pricing
All Photos(1)
About This Item
Linear Formula:
(NC)2C=C(CN)2
CAS Number:
Molecular Weight:
128.09
Beilstein:
1679885
EC Number:
MDL number:
UNSPSC Code:
12352117
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
![Dipyrazino[2,3-f:2′,3′-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile 95% (HPLC)](/deepweb/assets/sigmaaldrich/product/structures/151/558/c0e2c95f-5228-4864-a7a5-4b9765a19840/640/c0e2c95f-5228-4864-a7a5-4b9765a19840.png)
Quality Level
Assay
96%
reaction suitability
reagent type: oxidant
mp
197-199 °C (lit.)
storage temp.
2-8°C
SMILES string
N#CC(C#N)=C(C#N)C#N
InChI
1S/C6N4/c7-1-5(2-8)6(3-9)4-10
InChI key
NLDYACGHTUPAQU-UHFFFAOYSA-N
Looking for similar products? Visit Product Comparison Guide
Related Categories
Application
Used for postfunctional addition to polyphenylacetylene derivatives to change the oxygen permeability
Reactant for:
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
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 1 Oral - Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation
Storage Class Code
6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Customers Also Viewed
Siham Y Alqaradawi et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 71(4), 1594-1598 (2008-08-12)
The solid charge-transfer complexes formed in the reaction of the electron donor 1,4,7-trimethyl-1,4,7-triazacyclononane (TMTACN) with the acceptors iodine, tetracyanoethylene (TCNE) and 7,7,8,8-tetracyanoquinodimethane (TCNQ) have been isolated. These were characterized through electronic and infrared spectra as well as thermal and elemental
Dane Tomasino et al.
The Journal of chemical physics, 138(9), 094506-094506 (2013-03-15)
We have studied the pressure-induced physical and chemical transformations of tetracyanoethylene (TCNE or C6N4) in diamond anvil cells using micro-Raman spectroscopy, laser-heating, emission spectroscopy, and synchrotron x-ray diffraction. The results indicate that TCNE in a quasi-hydrostatic condition undergoes a shear-induced
Styliana I Mirallai et al.
The Journal of organic chemistry, 78(17), 8655-8668 (2013-07-31)
Eight 2-phenyl-3H-imidazo[4,5-b]quinoline-9-carbonitriles 15 are prepared in four steps from N'-arylbenzamidines 11 and tetracyanoethylene (TCNE) in ~70-90% yields. The transformation involves the initial formation of N-aryl-N'-(1,2,2-tricyanovinyl)benzamidines 12 in 87-99% yields, which in MeCN undergo a 5-exodig cyclization to give the 2-[1-aryl-5-imino-2-phenyl-1H-imidazol-4(5H)-ylidene]malononitriles
Mathieu Auzias et al.
Organic letters, 13(3), 474-477 (2010-12-22)
Complex tetracyclic ring systems were assembled by a photoinduced rearrangement of 3,3'-bis(arylbenzofurans). Irradiation of 1 under N(2) atmosphere yielded the benzonaphthofurans 2 in 75-90% yield. When the reaction was conducted under an O(2) atmosphere in the presence of tetracyanoethylene (TCNE)
Click-type reaction of aromatic polyamines for improvement of thermal and optoelectronic properties.
Tsuyoshi Michinobu
Journal of the American Chemical Society, 130(43), 14074-14075 (2008-10-07)
A quantitative addition reaction between aromatic amino-substituted alkynes and tetracyanoethylene (TCNE), yielding donor-substituted tetracyanobutadiene chromophores, was for the first time employed as a click-type reaction to improve the thermal and optoelectronic properties of aromatic polyamines. The first reduction potentials or
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service