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T8809

Sigma-Aldrich

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
Beilstein:
1679885
EC Number:
211-578-0
MDL number:
MFCD00001850
UNSPSC Code:
12352117
PubChem Substance ID:
24900563
NACRES:
NA.22

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

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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

Signal Word

Danger

Hazard Statements

H300,H312 + H332

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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)
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