Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

T8809

Sigma-Aldrich

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:
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

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:
  • 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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 2

1 of 2

1,4-Dicyanobenzene 98%

Sigma-Aldrich

D76722

1,4-Dicyanobenzene

Tetramethyltetraselenafulvalene 97%

Sigma-Aldrich

274402

Tetramethyltetraselenafulvalene

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
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
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
View All Related Papers

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