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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
Assay:
96%
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Quality Level

100

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

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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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)
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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Global Trade Item Number

SKUGTIN
T8809-5G04061837379727
T8809-25G04061835559879