Tetramethylsuccinonitrile

Base Information

• Chemical Name: Tetramethylsuccinonitrile
• CAS No.: 3333-52-6
• Molecular Formula: C8H12 N2
• Molecular Weight: 136.197
• European Community (EC) Number: 608-859-9
• ICSC Number: 1121
• NSC Number: 39746
• UN Number: 3439,2811
• UNII: 116XMU2GHK
• DSSTox Substance ID: DTXSID0026125
• Nikkaji Number: J48.683C
• Wikipedia: Tetramethylsuccinonitrile
• Wikidata: Q7706592
• ChEMBL ID: CHEMBL3182970
• Mol file: 3333-52-6.mol

Synonyms:tetramethylsuccinonitrile;TMSN

Chemical Property of Tetramethylsuccinonitrile

Chemical Property:

• Melting Point: 168°C
• Refractive Index: 1.4436 (estimate)
• Boiling Point: 264.2°Cat760mmHg
• Flash Point: 116.4°C
• PSA: 47.58000
• Density: 0.923g/cm³
• LogP: 2.08596
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Insoluble in water
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 136.100048391
• Heavy Atom Count: 10
• Complexity: 192
• Transport DOT Label: Poison

Purity/Quality:

98% ^*data from raw suppliers

2,2,3,3-Tetramethylsuccinonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Toxic by inhalation and skin contact. TLV: 0.5 ppm.
• Hazard Codes: T
• Statements: 23/24/25-36/37/38-48/20/21
• Safety Statements: 26-36/37/39-45-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: CC(C)(C#N)C(C)(C)C#N
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Short Term Exposure: The substance may cause effects on the central nervous system. Exposure at high concentrations could cause death.
• Uses: Blowing agent for vinyl foam production. 2,2,3,3-Tetramethylsuccinonitrile is used in preparation of 4,5-Dihydro-1,2,3-triazole derivatives as Farnesyltransferase inhibitors. 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.

Technology Process of Tetramethylsuccinonitrile

There total 36 articles about Tetramethylsuccinonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

2,2'-azobis(isobutyronitrile) (78-67-1) + {[(difluoromethyl)selanyl]methyl}benzene + 4-methyl-benzaldehyde (104-87-0) → Isobutyronitrile (78-82-0) + 2,2,3,3-tetramethylsuccinonitrile (3333-52-6) + Se-(difluoromethyl) 4-methylbenzoselenoate

Guidance literature:

In 1,2-dichloro-ethane; at 50 ℃; for 24h; Inert atmosphere;

DOI:10.1039/d0cc02912b

Reference yield: 74.0%

1-hexene (592-41-6,25067-06-5) + 2,2'-azobis(isobutyronitrile) (78-67-1) + diethyl iodomethanephosphonate (10419-77-9) → 2,2,3,3-tetramethylsuccinonitrile (3333-52-6) + Diethyl methylphosphonate (683-08-9) + tetraethyl ethylenebis(phosphonate) (995-32-4) + diethyl 3-iodo-n-heptylphosphonate

Guidance literature:

In benzene; at 80 ℃; for 6.5h; Further Variations:; Reaction partners; Reagents; Product distribution;

DOI:10.1039/b005882n

Reference yield: 53.0%

2,2'-azobis(isobutyronitrile) (78-67-1) → Isobutyronitrile (78-82-0) + dimethyl-N-(2-cyano-2-propyl)ketenimine (10551-67-4) + 2,2,3,3-tetramethylsuccinonitrile (3333-52-6) + N-(1-cyano-1-methylethyl)-2-methylpropanamide (84213-57-0)

Guidance literature:

With silica gel; at 10 ℃; Product distribution; Irradiation; further in benzene, D-labelled, var. conditions of irradiation;

DOI:10.1039/c39820001106

upstream raw materials:

2,2'-azobis(isobutyronitrile)

phenylmethanethiol

toluene

octane-2-thiol

Downstream raw materials:

tetramethylsuccinic anhydride

tetramethyl succinic acid

vanadyl(IV) phthalocyanine

Refernces

• 1、 Yamago, Shigeru,Iida, Kazunori,Nakajima, Mitsuru,Yoshida, Jun-Ichi. "Practical protocols for organotellurium-mediated living radical polymerization by in situ generated initiators from AIBN and ditellurides". . p. 3793 - 3796. Retrieved 2003.
• 2、 Guo, Rui-Li,Zhu, Xue-Qing,Zhang, Xing-Long,Wang, Yong-Qiang. "Synthesis of difluoromethylselenoesters from aldehydes: Via a radical process". supporting information. p. 8976 - 8979. Retrieved 2020/08/17.