Tetracyanoethylene

• Catalog No.: A13945
• CAS Number: 670-54-2
• M. F.: C6N4
• M. W.: 128.091
• Purity: 98%

SYNONYMS

• Title: 四氰基乙烯
• IUPAC name: eth-1-ene-1,1,2,2-tetracarbonitrile
• IUPAC Traditional name: tetracyanoethylene

DATABASE IDS

• Beilstein Number: 1679885
• Merck Index: 149195
• EC Number: 211-578-0
• MDL Number: MFCD00001850
• CAS Number: 670-54-2

PROPERTIES

• Purity: 98%
• Boiling Point: 223°C
• Density: 1.348
• Melting Point: 197-199°C
• GHS Hazard statements: H300-H310-H315-H319-H335
• European Hazard Symbols: Highly toxic (T+)
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P361-P405-P501A
• Risk Statements: 24-28-36/37/38
• RTECS: KM7300000
• Safety Statements: 20-26-27/28-36/37-45
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是
• Hazard Class: 6.1
• UN Number: UN3439
• Packing Group: II

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).