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670-54-2 - Tetracyanoethylene, 98% - A13945 - Alfa Aesar

A13945 Tetracyanoethylene, 98%

CAS Number
670-54-2
Synonyms

Size Price ($) Quantity Availability
1g 21.69
5g 60.93
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Tetracyanoethylene, 98%

MDL
MFCD00001850
EINECS
211-578-0

Chemical Properties

Formula
C6N4
Formula Weight
128.09
Melting point
197-199°
Boiling Point
223°
Density
1.348
Sensitivity
Moisture Sensitive
Solubility
Soluble in methanol, benzene, toluene, water (hydrolyses to form HCN), and ether (slightly).

Applications

Used for postfunctional addition to polyphenylacetylene derivatives to change the oxygen permeability. As reactant for Regioselective [2+2] cycloaddition reaction for production of BODIPY dyes2 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.

Notes

Moisture Sensitive. Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Store away from strong oxidizing agents.

Literature References

Masakazu Morimoto,; Kimie Murata,; Tsuyoshi Michinobu. Photochemical control of a highly efficient addition reaction between electron-rich alkynes and tetracyanoethylene.. Chemical Communications. 2011 47 (35), 9819-9821.

Songlin Niu,; Gilles Ulrich,; Pascal Retailleau,; Raymond Ziessel. Regioselective synthesis of 5-monostyryl and 2-tetracyanobutadiene BODIPY dyes. Organic Letters, 2011, 13 (19), 4996-4999.

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).

GHS Hazard and Precautionary Statements

Hazard Statements: H300-H310-H315-H319-H335

Fatal if swallowed. Fatal in contact with skin. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P262-P280-P301+P310-P305+P351+P338-P361-P302+P350-P304+P340-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Do not get in eyes, on skin, or on clothing. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Remove/Take off immediately all contaminated clothing. IF ON SKIN: Gently wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,9195
Beilstein
1679885
Hazard Class
6.1
Packing Group
II
Harmonized Tariff Code
2926.90
TSCA
Yes
RTECS
KM7300000

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