3566-61-8

Basic information

• Product Name: 3,3,4,4-tetramethylsuccinimide
• Synonyms: 3,3,4,4-tetramethylsuccinimide;2,2,3,3-Tetramethylsuccinimide;3,3,4,4-Tetramethylpyrrolidine-2,5-dione;3,3,4,4-TETRAMETHYLPYRROLIDINE-2,5-DIONE（WS200256）
• CAS NO: 3566-61-8
• Molecular Formula: C₈H₁₃NO₂
• Molecular Weight: 155.19
• Mol File: 3566-61-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 252.4°Cat760mmHg
• Flash Point: 108.5°C
• Appearance: /
• Density: 1.003g/cm³
• Vapor Pressure: 0.0194mmHg at 25°C
• Refractive Index: 1.439
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: 3,3,4,4-tetramethylsuccinimide(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3,4,4-tetramethylsuccinimide(3566-61-8)
• EPA Substance Registry System: 3,3,4,4-tetramethylsuccinimide(3566-61-8)

Safety Data

• Hazardous Substances Data: 3566-61-8(Hazardous Substances Data)

Usage

Description

3,3,4,4-tetramethylsuccinimide is an organic compound derived from the thermal decomposition of 2,2''-azobisisobutyramidine hydrochloride. It is characterized by its unique molecular structure and properties, which make it suitable for various applications across different industries.

Uses

Used in Chemical Synthesis:
3,3,4,4-tetramethylsuccinimide is used as an intermediate in the synthesis of various chemicals and pharmaceuticals due to its reactive nature and ability to undergo multiple chemical transformations.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3,3,4,4-tetramethylsuccinimide is used as a building block for the development of new drugs, particularly those targeting specific medical conditions. Its unique structure allows for the creation of novel molecular entities with potential therapeutic benefits.
Used in Material Science:
3,3,4,4-tetramethylsuccinimide is also utilized in the field of material science for the development of advanced materials with specific properties. Its incorporation into polymers and other materials can enhance their performance characteristics, such as strength, durability, and thermal stability.
Used in Research and Development:
Due to its unique chemical properties, 3,3,4,4-tetramethylsuccinimide is often employed in research and development settings to explore new reaction pathways, study its reactivity, and develop innovative applications in various fields.

InChI:InChI=1/C8H13NO2/c1-7(2)5(10)9-6(11)8(7,3)4/h1-4H3,(H,9,10,11)

Upstream product

• 666-52-4 [⁽²⁾H₆]acetone 
• 93588-79-5 tetrabutylammonium tetramethylsuccinimide - N-bromotetramethylsuccinimide complex 
• 99-99-0 1-methyl-4-nitrobenzene 
• 108-94-1 cyclohexanone 
• 67-64-1 acetone 
• 75-05-8 acetonitrile 
• 3842-20-4 N-(cyanomethyl)phthalimide 
• 112537-73-2 N-cyanomethyltetramethylsuccinimide 

Downstream Products

• 129277-84-5 tetrakis(tetramethylsuccinimido)-1,4-benzoquinone 
• 112537-75-4 N-acetonyltetramethylsuccinimide 
• 121900-41-2 N-(4-nitrobenzyl)tetramethylsuccinimide 
• 121900-43-4 2-(tetramethylsuccinimido)cyclohexanone 
• 35046-68-5 tetramethylsuccinic anhydride 
• 357672-67-4 3,3,4,4-tetramethyl-1-[2-(diphenylhydroxymethyl)thien-3-ylmethyl]succinimide 
• 200061-43-4 5-Hydroxy-3,3,4,4-tetramethyl-1-(2-phenyl-thiophen-3-ylmethyl)-pyrrolidin-2-one 
• 121900-44-5 α,β-dibromo-β-(tetramethylsuccinimido)styrene 
• 121900-47-8 phthalimido-bis(tetramethylcuccinimido)-acetonitrile 
• 112537-72-1 Tris-(3,3,4,4-tetramethyl-2,5-dioxo-pyrrolidin-1-yl)-acetonitrile 
• 145045-73-4 tert-Butyl 5-benzyloxycarbonyl-7-ethyl-2,2,3,3,8-pentamethyl-1-oxo-1,2,3,10-tetrahydrodipyrrin-9-carboxylate 

Relevant articles and documents

On the Reaction between the N-Bromotetramethylsuccinimide-Tetrabutylammonium Tetramethylsuccinimide Complex and C-H Acidic Compounds

The reaction between the N-bromotetramethylsuccinimide-tetrabutylammonium tetramethylsuccinimide complex and C-H acidic compounds has been studied.The main pathway leads to substitution of the acidic C-H bonds at the substrate by tetramethylsuccinimido groups, as exemplified by the formation of tris(tetramethylsuccinimido)acetonitrile from acetonitrile.The reaction with acetone is ca. 105 times faster than that with acetonitrile and displays a spectacular colour phenomenon: the initially colourless solution, after a reproducible and controllable induction period, suddenly becomes intensely purple, the absorbance maximum of which signals the end of the substitution process.Approximately in parallel with the colour development is the build-up and decay of an ESR signal (a 1:2:3:2:1 quintuplet).The position of the colour maximum can be used as a kinetic probe, the inverse of which has the dimensions of a first-order rate constant.Using this parameter, it has been established that the reaction is approximately first order in acetone, has a kinetic deuterium isotope effect of ca. 5, and has a rate-determining step involving attack of base upon the substrate.The reaction is autocatalytic with respect to the primary product, N-acetonyltetramethylsuccinimide (reaction order ca. 0.5), and is catalysed by a number of added bases, corresponding to conjugated acids of pK in the range 7-23.The mechanism most probably consists of an initial attack by tetramethylsuccinimide anion upon an acidic hydrogen of the substrate, followed by bromination of the enolate ion by the N-bromo imide.The bromo derivative reacts rapidly with tetramethysuccinmide anion to give the substitution product.The purple colour and the ESR signal are due to species originating from further reactions of the primary products.