CAS 670-54-2|Tetracyanoethylene|2,3-Dicyanobut-2-ene-1,4-dinitrile|eth-1-ene-1,1,2,2-tetracarbonitrile|tetracyanoethylene|Ethene-1,1,2,2-tetracarbonitrile|Ethylenetetracarbonitrile|四氰基乙烯|TETRAC...

General Information

Structure

Molecular Formula

C₆N₄

Molecular Mass

128.091

Exact Mass

128.01229602

Charge

InChI

InChI=1S/C6N4/c7-1-5(2-8)6(3-9)4-10

InChIKey

NLDYACGHTUPAQU-UHFFFAOYSA-N

Canonic Smiles

N#CC(=C(C#N)C#N)C#N

Isomeric Smiles

N#CC(=C(C#N)C#N)C#N

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

0.03203398

LogD (pH = 7.4)

0.03203398

Log P

0.03203398

Molar Refractivity

32.6728

Polarizability

11.009124

Polar Surface Area

95.16

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

Tetracyanoethylene2,3-Dicyanobut-2-ene-1,4-dinitrileEthene-1,1,2,2-tetracarbonitrileEthylenetetracarbonitrile四氰基乙烯TETRACYANOETHYLENEPercyanoethyleneTetracyanoethylene四氰基代乙烯TCNENSC 24833四氰乙烯eth-1-ene-1,1,2,2-tetracarbonitrile四氰基乙烯

IUPAC name

eth-1-ene-1,1,2,2-tetracarbonitrile

IUPAC Traditional name

tetracyanoethylene

Names and Identifiers

Registration numbers

EC Number

MDL Number

Beilstein Number

CAS Number

PubChem SID

2490056316204437324888858

PubChem CID

Chemspider ID

Wikipedia Title

Merck Index

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

05219182

MP Biomedicals Rare Chemical collection

Wikipedia

Tetracyanoethylene

Sigma Aldrich

T8809

Packaging
5, 25 g in glass bottle
Application
Used for postfunctional addition to polyphenylacetylene derivatives to change the oxygen permeability1Reactant for:
• Regioselective [2+2] cycloaddition reaction for production of BODIPY dyes2 and TCBD derivatives3
• Thermal addition reaction with alkynes4
• One-pot reactions with nucleophilic reagents forming aromatic cyanovinyl compounds5
• Synthesis of cobalt tetracyanoethylene films6
• Biotransformation by Botrytis cinerea7

87120

Other Notes
Powerful dienophile for cycloaddition reactions, reviews8,9
Application
Used for postfunctional addition to polyphenylacetylene derivatives to change the oxygen permeability1Reactant for:
• Regioselective [2+2] cycloaddition reaction for production of BODIPY dyes2 and TCBD derivatives3
• Thermal addition reaction with alkynes4
• One-pot reactions with nucleophilic reagents forming aromatic cyanovinyl compounds5
• Synthesis of cobalt tetracyanoethylene films6
• Biotransformation by Botrytis cinerea7

Molecule Details

References

PubChem Literature

From Data Sources

• π-Acid catalyst, compare DDQ (2,3-Dichloro-5,6-dicyanobenzoquinone, A11879) for the rearrangement of epoxides to ketones, formation of acetonides (1,3-dioxolanes) by reaction of epoxides with acetone: Chem. Lett., 17 (1993), formation of epoxides with hydrogen peroxide: Chem. Pharm. Bull., 43, 686 (1995), and for stereospecific alcoholysis of epoxides under mild conditions: Synlett, 847 (1993). In the presence of pyridine, carboxylic acids are converted to anhydrides: Tetrahedron Lett., 26, 1503 (1985). In an alcohol as solvent, catalyzes esterification and transesterification reactions: Chem. Lett., 55 (1997).

• Also catalyzes the carbon-carbon bond formation reactions of aldehydes, ketones and acetals with silylated nucleophiles including Trimethylsilyl cyanide, A19598, allyltrimethylsilane, silyl enol ethers and triethylsilane: J. Chem. Soc., Perkin 1, 2155 (1995).

• Versatile reagent and reactive dienophile. Reviews: Miscellaneous chemistry: Chem. Rev., 67, 611 (1967); Synthesis, 249 (1986); Addition and cycloaddition reactions: Synthesis, 749 (1987); Organometallic chemistry: Synthesis, 959 (1987).

References

Bioactivity

PubChem BioAssay

Bioactivity