Tetramethylsuccinonitrile

Chemical Properties

Colorless, solid; odorless. Insoluble in water.

Uses

Blowing agent for vinyl foam production.

Uses

2,2,3,3-Tetramethylsuccinonitrile is used in preparation of 4,5-Dihydro-1,2,3-triazole derivatives as Farnesyltransferase inhibitors.

Uses

2,2,3,3-Tetramethylsuccinonitrile can be used as a reactant to synthesize:

• 3,4-Dihydro-3H-pyrrol-2-imines by reacting with aryl lithium species in the presence of TMSCl.
• Phenyl substituted metal-free fused tetraazachlorins by condensation reaction with substituted phthalonitrile derivatives in the presence of InCl₃.

Synthesis Reference(s)

Journal of the American Chemical Society, 87, p. 4403, 1965 DOI: 10.1021/ja00947a046

General Description

White crystals.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Nitriles, such as TETRAMETHYLSUCCINONITRILE, may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids. TETRAMETHYLSUCCINONITRILE can react violently with (LiAlH4 + H2O).

Hazard

Toxic by inhalation and skin contact. Headache, nausea, and central nervous system convulsions.

Fire Hazard

Flash point data are not available for TETRAMETHYLSUCCINONITRILE, but TETRAMETHYLSUCCINONITRILE is probably combustible.

Safety Profile

Poison by ingestion, intraperitoneal, and intravenous routes. An experimental teratogen. A human skin irritant and allergen. In the preparation of sponge rubber, an azo compound is used that decomposes to form tetramethylsuccinonitrile or TMSN. Rats exposed to a concentration of 90 ppm exhbit their first convulsion after 1.5-2 hours or less. Rats exposed to concentration of 5.5 pprn exhbited their first convulsions in 27-31 hours and were dead in 31-46 hours. Absorbed by skin. The fatal dose in humans is thought to be about 25 mg/kg of body weight. TSN is slowly detoxified by the body. This nitrile is different from other nitriles in that duosulfate is a poor antidote for intoxication. When heated to decomposition it emits toxic fumes of CNand NOx. See also NITRILES and CYANIDE.