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Merck
CN

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:
670-54-2
Molecular Weight:
128.09
UNSPSC Code:
12352117
NACRES:
NA.22
PubChem Substance ID:
24900563
EC Number:
211-578-0
Beilstein/REAXYS Number:
1679885
MDL number:
MFCD00001850

Key Documents

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Product Name

Tetracyanoethylene, 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

100

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Related Categories

Application

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

pictograms

Skull and crossbones
GHS06

signalword

Danger

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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Certificates of Analysis (COA)

Lot/Batch Number
STBL4799
STBL1447
STBL2114
STBJ7975
STBG6784

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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
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
Cat Chenal et al.
Chemphyschem : a European journal of chemical physics and physical chemistry, 9(11), 1617-1623 (2008-07-10)
We explore the application of a previously suggested formula for determining the degree of charge transfer in surface-enhanced Raman scattering (SERS). SERS is often described as a phenomenon which obtains its enhancement from three major sources, namely the surface plasmon
Yongrong Li et al.
Macromolecular rapid communications, 32(22), 1804-1808 (2011-09-10)
A highly colored polystyrene derivative bearing side chain chromophores composed of dialkylanilino donor and cyano-based acceptor groups, prepared by atom-economic click postfunctionalization, displays the dual colorimetric detection behavior of several metal ions based on the specific interactions with different nitrogen
Christopher A Rumble et al.
Physical chemistry chemical physics : PCCP, 21(22), 11797-11809 (2019-05-23)
The structural dynamics of an electron donor/acceptor complex (DAC) consisting of benzene and tetracyanoethylene (Bz/TCNE) solvated in CH2Cl2 have been investigated using ultrafast spectroscopy and mixed quantum/classical computer simulations. Population dynamics from visible and infrared transient absorption (TRIR) spectroscopy point
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