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

• ChemBase ID: 79610
• Molecular Formular: C6N4
• Molecular Mass: 128.091
• Monoisotopic Mass: 128.01229602
• 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 670-54-2
• EC Number: 211-578-0
• MDL Number: MFCD00001850
• Beilstein Number: 1679885
• Merck Index: 149195
• PubChem SID: 162044373; 24900563; 24888858
• PubChem CID: 12635
• Chemspider ID: 12114
• Wikipedia Title: Tetracyanoethylene

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 0.03203398
• LogD (pH = 7.4): 0.03203398
• Log P: 0.03203398
• Molar Refractivity: 32.6728 cm^3
• Polarizability: 11.009124 Å^3
• Polar Surface Area: 95.16 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 197 - 199°C; 197-199 °C(lit.); 197-199°C; 197-200 °C; 197-200°C; 199 °C
• Boiling Point: 130-140 °C, 0.1 mm Hg (sublimes); 223°C; 223°C
• Density: 1.348; g/cm^3
• Hydrophobicity(logP): -1.88

Safety Information

• Storage Warning: Moisture Sensitive; Very Toxic/Moisture Sensitive/Store under Argon/Keep Cold
• RTECS: KM7300000
• European Hazard Symbols: Highly toxic (T+); Harmful (Xn)
• UN Number: 2811; UN3439
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 1; II
• Risk Statements: 20/21-28; 24-28-36/37/38; R:22
• Safety Statements: 20-26-27/28-36/37-45; 28-36/37-45; S:36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H310-H315-H319-H335; H300-H312-H332
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P361-P405-P501A; P264-P280-P301 + P310
• 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
• RID/ADR: UN 2811 6.1/PG 1
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (N); 95%; 95+%; 98%
• Grade: purum
• Linear Formula: (NC)2C=C(CN)2

DETAILS

MP Biomedicals - 05219182

MP Biomedicals Rare Chemical collection

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

Sigma Aldrich - 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

REFERENCES

• 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).