Succinimide
[CAS# 123-56-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amide
• Name: Succinimide
• Synonyms: Succinic imide; Succinic acid imide; Butanimide; 2,5-Dioxopyrrolidine; 2,5-Diketopyrrolidine; 2,5-Pyrrolidinedione
• Molecular Formula: C₄H₅NO₂
• Molecular Weight: 99.09
• CAS Registry Number: 123-56-8
• EC Number: 204-635-6
• SMILES: C1CC(=O)NC1=O

Properties

• Density: 1.41 g/mL (Expl.)
• Melting point: 123-125 °C (Expl.)
• Index of Refraction: 1.479 Calc.
• Boiling point: 285-290 °C (Expl.)
• Flash point: 201 °C (Expl.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

Succinimide, a cyclic imide with the chemical formula C₄H₅NO₂, is an organic compound of significant industrial and pharmaceutical importance. It was first isolated in the 19th century during studies on organic acids and their derivatives. Its structure, characterized by a five-membered ring containing nitrogen, provides unique chemical properties, including high thermal stability and reactivity under specific conditions, which have contributed to its widespread use in various fields.

The discovery of succinimide is closely tied to advancements in organic chemistry and the systematic study of carboxylic acid derivatives. Its synthesis involved the dehydration of succinic acid, a naturally occurring dicarboxylic acid, to form the imide. This reaction highlighted its potential for diverse chemical transformations and applications. The ability of succinimide to act as both a donor and acceptor of hydrogen bonds allows it to participate in various chemical processes, making it valuable in synthesis and material sciences.

Succinimide finds extensive applications in the pharmaceutical industry, where it is used as a precursor for the synthesis of drugs. It serves as a core structure in anticonvulsant medications such as ethosuximide, which is employed in the treatment of epilepsy. Additionally, its derivatives have been explored for their antimicrobial and anti-inflammatory properties, broadening its medical relevance.

In materials science, succinimide is used as a building block in the production of polymers, including polyimides, known for their high thermal resistance and mechanical strength. These materials are crucial in electronics, aerospace, and automotive industries. Succinimide also serves as a reagent in analytical chemistry, particularly in the synthesis of N-hydroxysuccinimide (NHS), which is widely used in bioconjugation and protein labeling techniques.

The versatility of succinimide highlights its importance as a chemical building block in science and industry. Its continued exploration and application demonstrate the enduring significance of fundamental organic compounds in advancing modern technology and healthcare.

References

1984. 2-Pyrrolidinone and succinimide endogenously present in several mammalian species. Life Sciences.
DOI: 10.1016/0024-3205(84)90461-2

1986. Metabolism of a synthetic L-isoaspartyl-containing hexapeptide in erythrocyte extracts. Enzymatic methyl esterification is followed by nonenzymatic succinimide formation. The Journal of Biological Chemistry.
DOI: 10.1016/s0021-9258(17)42470-7

2014. Highly Enantioselective Michael Addition Promoted by a New Diterpene-Derived Bifunctional Thiourea Catalyst: A Doubly Stereocontrolled Approach to Chiral Succinimide Derivatives. Chirality.
DOI: 10.1002/chir.22279