74830-30-1

Usage

Uses

Used in Organic Synthesis:
TETRABUTYLAMMONIUM SUCCINIMIDE is used as a catalyst and reagent in organic synthesis for its ability to promote reactions with the succinimide anion in aprotic, organic solvents. This allows for the efficient synthesis of various organic compounds and the formation of desired products with improved yields and selectivity.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, TETRABUTYLAMMONIUM SUCCINIMIDE is used as a key intermediate in the synthesis of various drug molecules. Its unique properties enable the development of new drugs with improved pharmacological profiles and therapeutic applications.
Used in Chemical Research:
TETRABUTYLAMMONIUM SUCCINIMIDE is utilized as a research tool in chemical laboratories for studying reaction mechanisms, exploring new synthetic routes, and developing innovative methodologies in organic chemistry. Its ability to stabilize the succinimide anion in aprotic solvents makes it a valuable asset in advancing scientific knowledge and discovering new chemical reactions.

InChI:InChI=1/C16H36N.C4H5NO2/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;6-3-1-2-4(7)5-3/h5-16H2,1-4H3;1-2H2,(H,5,6,7)/q+1;/p-1

Upstream product

• 123-56-8 Succinimide 
• 1643-19-2 tetrabutylammomium bromide 
• 32503-27-8 tetra(n-butyl)ammonium hydrogensulfate 

Downstream Products

• 541-59-3 maleiimide 
• 123-56-8 Succinimide 
• 3470-96-0 N-butylsuccinimide 
• 102-82-9 tributyl-amine 

Relevant academic research and scientific papers

Polymaleinimide Formation in the Electron Transfer Reaction Between N-Bromosuccinimide and Succinimide Anion

The electron transfer reaction between N-bromosuccinimide (SBr) and succinimide anion (S-) gives predominantly succinimide (SH, ca. 65 percent) but also a small percentage (ca. 10 percent) of a polymeric material, the nature of which has now been elucidated.By NMR spectral comparison with authentic specimens, the polymer was shown to be of the polymaleinimide type.The build-up and decay of maleinimide during the SBr/S- reaction could be followed (NMR).Also, the development of the characteristic, base-induced yellow-red coulor of polymaleinimide could be followed kinetically and the effect of additives studied.Finally, the SBr/S- reaction exhibited weak chemiluminescence.These findings further strengthen the hypothesis that the initial step of the reaction is ET between SBr and S-, forming a cage radical ion/radical pair.Nitrogen-bromine bond cleavage within the cage produces a pair of S*, which react with disproportionation to give SH and maleinimide.The latter then undergoes predominant radical polymerization.The reaction between N-chlorosuccinimide and S- also gave polymaleinimide (40 percent) in addition to SH (47 percent).

Electrochemical Reduction of N-Bromosuccinimide. Reaction Mechanism for Formation of the Succinimidyl Radical

The electrochemical reduction of N-bromosuccinimide in acetonitrile at a platinum cathode generates the succinimidyl radica;l in an overall process for which the n value is 1.The succinimide anion, generated by two-electron reduction of N-bromosucinimide, is an intermediate in this process, and its electron-transfer reaction with the N-bromo imide generates the radical.The intermediacy of the succinimide anion is demonstrated by trapping experiments in which the anion is captured by alkylating agents to give N-alkylsuccinimides.With increasing capture of the anion the n value for the electrochemical reaction approaches 2 as a limit.The reduction of N-bromosuccinimide by the succinimide anion, added as a quaternary ammonium succinimide, in a purely chemical system has also been studied.Rate constants for the pertinent reactions have been measured, and the reaction mechanisms have been discussed.