Catalog Number
ACMA00017191
IUPAC Name
pyrrolidine-2,5-dione
Molecular Weight
99.09g/mol
Canonical SMILES
C1CC(=O)NC1=O
InChI
InChI=1S/C4H5NO2/c6-3-1-2-4(7)5-3/h1-2H2,(H,5,6,7)
InChI Key
KZNICNPSHKQLFF-UHFFFAOYSA-N
Application
Succinimide serves as a versatile chemical reagent with broad applications in industrial and organic synthesis processes. Primarily known for its role in silver plating, succinimide is integral in the synthesis of Lumiflavin, a photolysis product of vitamin B2. Additionally, it facilitates the formation of covalent bonds between proteins, peptides, and plastics. This compound is also crucial in the synthesis of heterocyclic compounds through N-acyliminium cyclizations. It is characterized as a dicarboximide, derived from pyrrolidine with oxo groups at specific positions, and it naturally occurs in certain plants like Xanthium strumarium and Panax notoginseng. Succinimide appears as a white crystalline powder, easily dissolving in water, alcohol, or sodium hydroxide, while remaining insoluble in ether and chloroform.
Covalently-Bonded Unit Count
1
EC Number
204-635-6;209-537-7
MeSH Entry Terms
2,5-diketopyrrolidine;succinimide;succinimide calcium salt;succinimide gold potassium salt;succinimide mercury salt;succinimide silver potassium salt;succinimide silver salt;succinimide silver salt (+2);succinimide sodium salt
Monoisotopic Mass
99.032028g/mol
NSC Number
49152;41221;38417;13114;11204
Vapor Pressure
7.50e-05 mmHg