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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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