3333-52-6

Basic information

• Product Name: TETRAMETHYLSUCCINONITRILE
• Synonyms: 2,2,3,3-Tetramethylsuccinonitrile;Butanedinitrile, tetramethyl-;butanedinitrile,tetramethyl-;Butanedinitrile,tetramethyl-(9CI);cp75475;Succinonitrile, tetramethyl-;succinonitrile,tetramethyl-;tetramethyl-butanedinitril
• CAS NO: 3333-52-6
• Molecular Formula: C₈H₁₂N₂
• Molecular Weight: 136.19
• EINECS: 604-604-1
• Product Categories: Dinitriles;Dinitriles & Trinitriles;Fine Chemicals
• Mol File: 3333-52-6.mol
• Article Data: 18

Chemical Properties

• Melting Point: 168°C
• Boiling Point: 240.49°C (rough estimate)
• Flash Point: 116.4°C
• Appearance: /
• Density: 1.0700
• Refractive Index: 1.4436 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water
• CAS DataBase Reference: TETRAMETHYLSUCCINONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: TETRAMETHYLSUCCINONITRILE(3333-52-6)
• EPA Substance Registry System: TETRAMETHYLSUCCINONITRILE(3333-52-6)

Safety Data

• Hazard Codes: T
• Statements: 23/24/25-36/37/38-48/20/21
• Safety Statements: 26-36/37/39-45-36/37
• RIDADR: 3439
• WGK Germany: 3
• RTECS: WN4025000
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 3333-52-6(Hazardous Substances Data)

Usage

Description

2,2,3,3-Tetramethylsuccinonitrile, also known as TETRAMETHYLSUCCINONITRILE, is an organic compound with the chemical formula C8H13N. It is a colorless liquid with a slight odor and is soluble in water. TETRAMETHYLSUCCINONITRILE is a versatile chemical intermediate used in the synthesis of various compounds and has applications in different industries.

Uses

Used in Vinyl Foam Production:
TETRAMETHYLSUCCINONITRILE is used as a blowing agent for vinyl foam production. It helps to create lightweight and flexible foam materials with improved insulation properties.
Used in Pharmaceutical Industry:
TETRAMETHYLSUCCINONITRILE is used in the preparation of 4,5-Dihydro-1,2,3-triazole derivatives, which act as Farnesyltransferase inhibitors. These inhibitors have potential applications in the treatment of various diseases, including cancer and neurodegenerative disorders.
Used in Organic Synthesis:
TETRAMETHYLSUCCINONITRILE can be used as a reactant to synthesize various organic compounds, such as 3,4-Dihydro-3H-pyrrol-2-imines by reacting with aryl lithium species in the presence of TMSCl. This reaction allows for the formation of new chemical entities with potential applications in various fields.
Used in the Synthesis of Metal-Free Fused Tetraazachlorins:
TETRAMETHYLSUCCINONITRILE can also be used in the synthesis of phenyl substituted metal-free fused tetraazachlorins by condensation reaction with substituted phthalonitrile derivatives in the presence of InCl3. These compounds have potential applications in the development of new materials with unique properties.

Synthesis Reference(s)

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

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.

Upstream product

• 78-67-1 2,2'-azobis(isobutyronitrile) 
• 3001-66-9 octane-2-thiol 
• 108-88-3 toluene 
• 111-88-6 Octanethiol 
• 19334-98-6 thiobenz-p-dimethylaminoanilide 
• 32294-60-3 diphenyl ditelluride 
• 592-41-6 1-hexene 
• 10419-77-9 diethyl iodomethanephosphonate 
• 1825-33-8 phenylazo-i-butyric acid nitrile 
• 126-98-7 methacrylonitrile 
• 26060-23-1 4-methoxy-N-phenylthiobenzamide 
• 53313-86-3 Bis-(isobutyronitril-2-azo-3'-isovaleroyl)-peroxid 
• 51655-69-7 Isobutyronitril-2-azo-3'-isovaleriansaeure-tert.-butylperester 
• 34241-39-9 azobisisobutyronitrile 

Downstream Products

• 35046-68-5 tetramethylsuccinic anhydride 
• 630-51-3 tetramethyl succinic acid 
• 78-82-0 Isobutyronitrile 
• 4645-35-6 octaphenyl-meso-tetraazaporphin 

Relevant articles and documents

Reductive Termination of Cyanoisopropyl Radicals by Copper(I) Complexes and Proton Donors: Organometallic Intermediates or Coupled Proton-Electron Transfer?

Cyanoisopropyl radicals, generated thermally by the decomposition of azobis(isobutyronitrile) (AIBN), participate in reductive radical termination (RRT) under the combined effect of copper(I) complexes and proton donors (water, methanol, triethylammonium salts) in acetonitrile or benzene. The investigated copper complexes were formed in situ from [CuI(MeCN)4]+BF4- in CD3CN or CuIBr in C6D6 using tris[2-(dimethylamino)ethyl]amine (Me6TREN), tris(2-pyridylmethyl)amine (TPMA), and 2,2′-bipyridine (BIPY) ligands. Upon keeping all other conditions constants, the impact of RRT is much greater for the Me6TREN and TPMA systems than for the BIPY system. RRT scales with the proton donor acidity (Et3NH+ a‰? H2O > CH3OH), it is reduced by deuteration (H2O > D2O and CH3OH > CD3OD), and it is more efficient in C6D6 than in CD3CN. The collective evidence gathered in this study excludes the intervention of an outer-sphere proton-coupled electron transfer (OS-PCET), while an inner-sphere PCET (IS-PCET) cannot be excluded for coordinating proton donors (water and methanol). On the other hand, the strong impact of RRT for the noncoordinating Et3NH+ in CD3CN results from the formation of an intermediate CuI-radical adduct, suggested by DFT calculations to involve binding via the N atom to yield keteniminato [L/Cu-N=C=CMe2]+ derivatives with only partial spin delocalization onto the Cu atom.

Solvent and external pressure effects on the ratio of the cyanoisopropyl radical recombination and disproportionation rates

A GC-MS analysis of the azobisisobutyronitrile thermal decomposition products of in solutions at 80 C showed that the ratio of recombination and disproportionation rates of the cyanoisopropyl radical does not depend on the medium viscosity, but increases when the internal pressure of the solvent increases according to the log(k dispr/k rec) = -1.25 + 0.096 P int 0.5 law. This means that the activation volume corresponding to recombination is larger than that corresponding to disproportionation. It follows from the relationship log(k dispr/k rec) = (ΔV rec ≠ - Δv dispr ≠)ΔP/RT that, for the decomposition of the substrate in benzene under a pressure of 0.5-4.0 kbar, the difference between the activation volumes is ΔV rec ≠ - ΔV dispr ≠ = 8 cm3/mol.

The Effect of Viscosity on the Diffusion and Termination Reaction of Organic Radical Pairs

The effect of viscosity on the diffusion efficiency (Fdif) of an organic radical pair in a solvent cage and the termination mechanism, that is, the selectivity of disproportionation (Disp) and combination (Comb) of the geminated caged radical pair and the diffused radicals encountered, were investigated quantitatively by following the photolysis of dimethyl 2,2′-azobis(2-methylpropionate) (V-601) in the absence and presence of PhSD. Fdif and Disp/Comb selectivity outside the cage [Disp(dif)/Comb(dif)] are highly sensitive to the viscosity. In contrast, the Disp/Comb selectivity inside the cage [Disp(cage)/Comb(cage)] is rather insensitive. The difference in viscosity dependence between Disp(cage)/Comb(cage) and Disp(dif)/Comb(dif) is explained by the spin state of the radical pair inside and outside the cage and the spin state dependent configurational changes of the radical pair upon their collision. Given that the configurational change of the radicals associates the displacement and reorganization of solvents around the radicals, the termination outside the cage, which requires larger change than that inside the cage, is highly viscosity dependent. Furthermore, while the bulk viscosity of each solvent shows good correlation with Fdif and Disp/Comb selectivity, microviscosity is the better parameter predicting Fdif and Disp(dif)/Comb(dif) selectivity regardless of the solvents.