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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:
670-54-2
Molecular Weight:
128.09
EC Number:
211-578-0
UNSPSC Code:
12352100
PubChem Substance ID:
24888858
Beilstein/REAXYS Number:
1679885
MDL number:
MFCD00001850
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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:
  • 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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