2,2,3,3-Tetramethylsuccinimide

Base Information

• Chemical Name: 2,2,3,3-Tetramethylsuccinimide
• CAS No.: 3566-61-8
• Molecular Formula: C8H13 N O2
• Molecular Weight: 155.197
• Hs Code.: 2925190090
• NSC Number: 74524
• UNII: YDF3PMM90Z
• DSSTox Substance ID: DTXSID20189164
• Nikkaji Number: J346.051G
• Wikidata: Q27294474
• Mol file: 3566-61-8.mol

Synonyms:3,3,4,4-tetramethylsuccinimide;TMSM

Chemical Property of 2,2,3,3-Tetramethylsuccinimide

Chemical Property:

• Vapor Pressure: 0.0194mmHg at 25°C
• Boiling Point: 252.4°Cat760mmHg
• Flash Point: 108.5°C
• PSA: 46.17000
• Density: 1.003g/cm³
• LogP: 1.02400
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 155.094628657
• Heavy Atom Count: 11
• Complexity: 204

Purity/Quality:

99%, ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C(=O)NC(=O)C1(C)C)C
• Uses: 2,2,3,3-Tetramethylsuccinimide is a product of the thermal decomposition of 2,2''-azobisisobutyramidine hydrochloride.

Technology Process of 2,2,3,3-Tetramethylsuccinimide

There total 9 articles about 2,2,3,3-Tetramethylsuccinimide 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: 68.0%

acetonitrile (75-05-8,26809-02-9) → 2,2,3,3-tetramethylsuccinimide (3566-61-8) + C12H21NO2 (112537-71-0) + Tris-(3,3,4,4-tetramethyl-2,5-dioxo-pyrrolidin-1-yl)-acetonitrile (112537-72-1)

Guidance literature:

for 45h; Heating;

Reference yield: 65.0%

N-(cyanomethyl)phthalimide (3842-20-4) → 2,2,3,3-tetramethylsuccinimide (3566-61-8) + phthalimido-bis(tetramethylcuccinimido)-acetonitrile (121900-47-8)

Guidance literature:

In benzene; Heating;

Reference yield: 59.0%

N-cyanomethyltetramethylsuccinimide (112537-73-2) → 2,2,3,3-tetramethylsuccinimide (3566-61-8) + Tris-(3,3,4,4-tetramethyl-2,5-dioxo-pyrrolidin-1-yl)-acetonitrile (112537-72-1)

Guidance literature:

In benzene; Heating;

upstream raw materials:

[⁽²⁾H₆]acetone

tetrabutylammonium tetramethylsuccinimide - N-bromotetramethylsuccinimide complex

1-methyl-4-nitrobenzene

cyclohexanone

Refernces

• 1、 Finkelstein, Manuel,Hart, Shirley A.,Moore, W. Michael,Ross, Sidney D.,Eberson, Lennart. "Facile Substitution of Aliphatic C-H Bonds by the Tetramethylsuccinimidyl Radical during Thermal Decomposition of the N-Bromotetramethylsuccinimide/Tetramethylsuccinimide Anion Complex". . p. 232 - 234. Retrieved 2007/10/02.