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123-56-8
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123-56-8
Succinimide, also known as 2,5-pyrrolidinedione, 2,5-dionepyrrolidine, succinic imide, has the chemical formula C4H5NO2, a molecular weight of 99.09, CAS number 123-56-8, EINECS 204-635-6, and UNII 10X90O3503. It is a cyclic imide of succinic acid (succinic acid), belonging to the class of cyclic imides. It is a white crystalline solid, obtained by the thermal decomposition of ammonium succinate, and is used in various organic synthesis processes and some industrial silver plating processes. With its comprehensive properties such as easy N-position functionalization, imide ring stability, and coordination complexation, succinimide is widely used in fine chemicals, surface treatment, lubrication, and scientific research: In fine chemicals, it is the parent material of N-functionalized succinimides such as N-bromosuccinimide (NBS), N-chlorosuccinimide (NCS), and N-hydroxysuccinimide (NHS); in surface treatment, it is a complexing and stabilizing component in industrial silver plating; in lubrication, it is the core structure of ashless dispersants in polyisobutylene succinimide (PIBSI) lubricating oils; and it is a cyclic imide intermediate used in fine chemicals, surface treatment, lubrication, and biotechnology.
Basic information : Chemical formula C4H5NO2, molecular weight 99.09; CAS number 123-56-8; EINECS 204-635-6; UNII 10X90O3503; EPA DSSTox DTXSID8051629; Merck Index 12th 9040; DrugBank DB13376; IUPAC name pyrrolidine-2,5-dione; Synonyms: succinimide, 2,5-pyrrolidinedione, 2,5-dionepyrrolidine, succinimide, butanimide, 2,5-dioxopyrrolidine.
Structure : Succinimide molecule is a five-membered ring: four atoms form a ring skeleton (two methylene + two carbonyl carbons), and the nitrogen atom connects to two carbonyl groups to form a cyclic imide (-CO-NH-CO-). NH has weak acidity (it can form salts with bases and can be replaced by halogens/N-hydroxyl groups, etc.).
Physically , succinimide is a white crystalline solid with a density of approximately 1.41 g/cm³. It is readily soluble in water (with good water solubility) and ethanol, and slightly soluble in nonpolar solvents such as ether and chloroform. Its aqueous solution is weakly acidic, and it easily sublimes upon heating.
Chemically , succinimide is a typical cyclic imide: NH is acidic (pKa approximately 9.5, can be deprotonated by strong bases to form salts); the N-position can be substituted by halogens to form N-halosuccinimides (NBS, NCS), substituted by hydroxyl groups to form N-hydroxysuccinimides (NHS), and substituted by alkyl groups to form N-alkylsuccinimides; it can form complexes with metal ions (such as silver complexes in electroplating); it can be hydrolyzed by heating with strong bases to open the ring and form succinic acid derivatives; the methylene group (3-position) on the ring has certain activity and can participate in condensation reactions.
plays an irreplaceable role in industrial, biotechnology, and scientific research fields due to its quadruple properties of "N-position functionalization + imide ring stabilization + coordination complexation + hydrophobic-lipophilic balance" .
N-position functionalization mechanism (NBS/NCS reagents) : The acidic hydrogen atom of succinimide NH can be replaced by halogens to generate N-bromosuccinimide (NBS) and N-chlorosuccinimide (NCS). The N-x bond homolytically cleaves to generate halogen radicals, which are standard reagents for reactions such as allylic/benzyl bromination, chlorination, and halolactoneation. They are widely used in fine chemical synthesis in industry and in laboratory organic synthesis and functionalization of complex molecules in scientific research.
Coordination complexation mechanism (silver plating and complex research) : The imine nitrogen and carbonyl group of the succinimide ring can coordinate with silver ions to form stable complexes, control the concentration of free silver ions in the plating bath, and achieve uniform and dense silver deposition. It is a complexation stabilizing component in cyanide-free/low-cyanide silver plating systems. The same coordination chemistry principle is also used in the synthesis of metal complexes and ligand research in scientific research.
Hydrophobic-lipophilic balance mechanism (lubricating oil additive) : The succinimide ring (polar head) combines with long-chain lipophilic groups (such as polyisobutylene chains) to form an amphiphilic structure, which is the core structure of polyisobutylene succinimide (PIBSI) type lubricating oil ashless dispersants. Its polar head adsorbs soot and sludge, and the lipophilic chains are suspended in the oil, preventing engine sludge deposition.
N-hydroxy activated ester mechanism (bioconjugation and scientific research) : A hydroxyl group is introduced at the N-position of succinimide to generate N-hydroxysuccinimide (NHS). NHS esters can form stable amide bonds with the amino groups of proteins/peptides, and are used for covalent coupling of proteins/peptides with plastics or labels. It is a classic activated ester system for protein labeling and immobilization in the fields of diagnostic kits in the biotechnology field and scientific research.
Application areas: Fine chemical reagents and organic synthesis.
Corresponding products: raw materials for the synthesis of N-bromosuccinimide (NBS), raw materials for the synthesis of N-chlorosuccinimide (NCS), raw materials for N-iodosuccinimide, raw materials for allyl bromide reagents, raw materials for benzylic halogenation reagents, raw materials for halolactoneation reagents, raw materials for oxidative halogenation reagents, halogenated intermediate reagents, etc.
Why it can be used in this way: The acidic hydrogen of succinimide NH is halogenated to generate N-halosuccinimide (NBS, NCS), and its NX bond is homolytically cleaved to generate halogen free radicals, which are standard reagents for allylic/benzyl bromination, chlorination and halolactoneation. Succinimide, as the parent material of NBS/NCS, is a key intermediate in fine chemical synthesis.
Application areas: Electroplating and surface treatment.
Corresponding products: silver plating bath complexing stabilizer, cyanide-free silver plating complexing agent, low-cyanide silver plating additive, silver alloy electroplating complexing agent, silver plating additive for electronic connectors, silver plating formula for tableware and jewelry, silver plating additive for reflectors, decorative silver plating complexing components, etc.
Why it can be used for this purpose: The imine nitrogen and carbonyl group of succinimide can coordinate with silver ions to form a stable complex, which controls the concentration of free silver in the plating solution, improves the uniformity and density of the coating, and is a complex stabilizing component in silver plating solution.
Application area: Lubricating oil additives.
Corresponding products: ashless dispersant intermediates for polyisobutylene succinimide (PIBSI), engine oil dispersant components, automatic transmission oil additives, marine lubricant dispersants, heavy-duty diesel engine oil dispersants, gasoline engine oil detergents and dispersants, lubricant compound components, synthetic lubricant additives (Lubrizol 6406 type), etc.
Why it works for this purpose: The succinimide ring (polar head) and the long-chain lipophilic group (such as polyisobutylene) form an amphiphilic structure, which is the core structure of polyisobutylene succinimide (PIBSI) type ashless dispersants. Its polar head adsorbs soot and sludge, and the lipophilic chain suspends it in the oil, preventing engine sludge deposition and viscosity increase.
Application areas: bioconjugation, diagnostic reagents and biotechnology.
Corresponding products: raw materials for the synthesis of N-hydroxysuccinimide (NHS), NHS activated ester intermediates, raw materials for protein coupling reagents, raw materials for peptide coupling reagents, raw materials for enzyme immobilization reagents, and biosensor coupling reagents, etc.
Why it can be used for this purpose: The introduction of a hydroxyl group at the N-position of succinimide generates N-hydroxysuccinimide (NHS). Its activated ester reacts with the amino group of protein/peptide to form a stable amide bond, realizing the covalent coupling of protein/peptide with plastics, labels or carriers . It is a classic activated ester system raw material for bioconjugation and diagnostic kits.
Application areas: Organic synthesis and chemical analysis.
Corresponding products include: organic synthesis imide reagents, analytical chemistry standards, metal complex research ligands, N-functionalized succinimide synthesis raw materials, chemical research intermediates, polymer modification research monomers, chromatographic analysis standards, and teaching experimental reagents.
Why it can be used for this purpose: Succinimide is a well-defined cyclic imide. The NH group can be functionalized, and the ring can participate in a variety of reactions (halogenation, N-alkylation, ring-opening hydrolysis). It is a basic reagent for laboratory organic synthesis, coordination chemistry research and analysis standards.
Succinimide (C4H5NO2, CAS 123-56-8, molecular weight 99.09) boasts a quadruple property of "N-position functionalization + imide ring stabilization + coordination complexation + hydrophobic-lipophilic balance," making it widely used in the synthesis of N-halogenated succinimides (NBS/NCS), industrial silver plating complexing agents, ashless dispersant intermediates for lubricating oils, raw materials for N-hydroxysuccinimides and bioconjugation reagents, and scientific reagents and organic synthesis standards. Among these, N-halogenated reagents (NBS/NCS) and industrial silver plating are its two main applications, while lubricating oil dispersants represent a high-value direction. The product is obtained by the thermal decomposition of ammonium succinate or the cyclization of succinic acid with ammonia. It is a white crystalline solid with a melting point of approximately 125-126℃, readily soluble in water and ethanol.
