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670-54-2 molecular structure
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eth-1-ene-1,1,2,2-tetracarbonitrile

ChemBase ID: 79610
Molecular Formular: C6N4
Molecular Mass: 128.091
Monoisotopic Mass: 128.01229602
SMILES and InChIs

SMILES:
N#CC(=C(C#N)C#N)C#N
Canonical SMILES:
N#CC(=C(C#N)C#N)C#N
InChI:
InChI=1S/C6N4/c7-1-5(2-8)6(3-9)4-10
InChIKey:
NLDYACGHTUPAQU-UHFFFAOYSA-N

Cite this record

CBID:79610 http://www.chembase.cn/molecule-79610.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
eth-1-ene-1,1,2,2-tetracarbonitrile
IUPAC Traditional name
tetracyanoethylene
Synonyms
TETRACYANOETHYLENE
Tetracyanoethylene
2,3-Dicyanobut-2-ene-1,4-dinitrile
Ethene-1,1,2,2-tetracarbonitrile
eth-1-ene-1,1,2,2-tetracarbonitrile
TCNE
NSC 24833
Ethylenetetracarbonitrile
Percyanoethylene
Tetracyanoethylene
四氰基乙烯
四氰基乙烯
四氰基代乙烯
四氰乙烯
CAS Number
670-54-2
EC Number
211-578-0
MDL Number
MFCD00001850
Beilstein Number
1679885
Merck Index
149195
PubChem SID
24888858
162044373
24900563
PubChem CID
12635
Chemspider ID
12114
Wikipedia Title
Tetracyanoethylene

CALCULATED PROPERTIES

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 cm3
Polarizability 11.009124 Å3 Polar Surface Area 95.16 Å2
Rotatable Bonds Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Melting Point
197 - 199°C expand Show data source
197-199 °C(lit.) expand Show data source
197-199°C expand Show data source
197-200 °C expand Show data source
197-200°C expand Show data source
199 °C expand Show data source
Boiling Point
130-140 °C, 0.1 mm Hg (sublimes) expand Show data source
223°C expand Show data source
223°C expand Show data source
Density
1.348 expand Show data source
g/cm3 expand Show data source
Hydrophobicity(logP)
-1.88 expand Show data source
Storage Warning
Moisture Sensitive expand Show data source
Very Toxic/Moisture Sensitive/Store under Argon/Keep Cold expand Show data source
RTECS
KM7300000 expand Show data source
European Hazard Symbols
Highly toxic Highly toxic (T+) expand Show data source
Harmful Harmful (Xn) expand Show data source
UN Number
2811 expand Show data source
UN3439 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
1 expand Show data source
II expand Show data source
Risk Statements
20/21-28 expand Show data source
24-28-36/37/38 expand Show data source
R:22 expand Show data source
Safety Statements
20-26-27/28-36/37-45 expand Show data source
28-36/37-45 expand Show data source
S:36/37/39 expand Show data source
TSCA Listed
expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H300-H310-H315-H319-H335 expand Show data source
H300-H312-H332 expand Show data source
GHS Precautionary statements
P261-P301+P310-P305+P351+P338-P361-P405-P501A expand Show data source
P264-P280-P301 + P310 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
RID/ADR
UN 2811 6.1/PG 1 expand Show data source
Storage Temperature
2-8°C expand Show data source
Purity
≥97.0% (N) expand Show data source
95% expand Show data source
95+% expand Show data source
98% expand Show data source
Grade
purum expand Show data source
Certificate of Analysis
Download expand Show data source
Linear Formula
(NC)2C=C(CN)2 expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
MP Biomedicals - 05219182 external link
MP Biomedicals Rare Chemical collection
Sigma Aldrich - T8809 external link
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
Sigma Aldrich - 87120 external link
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

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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).
  • • 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).
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PATENTS

PATENTS

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INTERNET

INTERNET

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