87120
Tetracyanoethylene
purum, ≥97.0% (N)
Synonym(s):
Ethylenetetracarbonitrile, NSC 24833, Percyanoethylene, TCNE
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About This Item
Linear Formula:
(NC)2C=C(CN)2
CAS Number:
Molecular Weight:
128.09
EC Number:
211-578-0
UNSPSC Code:
12352100
PubChem Substance ID:
Beilstein/REAXYS Number:
1679885
MDL number:
grade
purum
assay
≥97.0% (N)
mp
197-199 °C (lit.), 197-200 °C
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:
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
Other Notes
Powerful dienophile for cycloaddition reactions, reviews
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Synthesis, 749-749 (1987)
A.J. Fatiadi
Synthesis, 249-249 (1986)