T8809
Tetracyanoethylene
96%
Synonym(s):
Ethylenetetracarbonitrile, NSC 24833, Percyanoethylene, TCNE
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About This Item
Linear Formula:
(NC)2C=C(CN)2
CAS Number:
Molecular Weight:
128.09
UNSPSC Code:
12352117
NACRES:
NA.22
PubChem Substance ID:
EC Number:
211-578-0
Beilstein/REAXYS Number:
1679885
MDL number:
Assay:
96%
InChI key
NLDYACGHTUPAQU-UHFFFAOYSA-N
InChI
1S/C6N4/c7-1-5(2-8)6(3-9)4-10
SMILES string
N#CC(C#N)=C(C#N)C#N
assay
96%
reaction suitability
reagent type: oxidant
mp
197-199 °C (lit.)
storage temp.
2-8°C
Quality Level
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
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 1 Oral - Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation
Storage Class
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
ppe
Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
Regulatory Information
危险化学品
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Gerasimos S Armatas et al.
Journal of the American Chemical Society, 130(34), 11430-11436 (2008-08-06)
We report the surfactant-directed assembly of mesoporous metal/germanium-based semiconducting materials from coupling of anionic (Ge 9) (4-) clusters with various linking metal ions. The resulting materials feature a metal/Ge 9 framework perforated by regular arrays of mesoporous channels. The permanent
Milan Kivala et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 14(25), 7638-7647 (2008-07-22)
A series of monomeric and oligomeric donor-substituted 1,1,4,4-tetracyanobuta-1,3-dienes (TCBDs) with various topologies have been synthesized by means of thermal [2+2] cycloaddition between tetracyanoethylene (TCNE) and donor-substituted alkynes, followed by retro-electrocyclization. One-electron-reduced and -oxidized stages of the donor-substituted TCBDs were generated
Matthew Mudge et al.
Chemphyschem : a European journal of chemical physics and physical chemistry, 15(17), 3776-3781 (2014-09-13)
The crystal structure of pentamethylbenzene has been obtained for the first time with the use of synchrotron radiation, whilst the low-energy spectrum of lattice dynamics, dominated by the methyl group torsions, was obtained using inelastic neutron scattering. The effect of
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
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
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