N-(N-Benzyloxycarbonyloxy)succinimide

• CAT Number: R020958
• CAS Number: 13139-17-8
• Molecular Formula: C12H11NO5
• Molecular Weight: 249.22
• Purity: ≥95%
• Synonyms: 1-[[(Benzyloxy)carbonyl]oxy]-2,5-pyrrolidinedione; 1-[[(Phenylmethoxy)carbonyl]oxy]-2,5-pyrrolidinedione; 1-[[[(Phenylmethyl)oxy]carbonyl]oxy]-2,5-pyrrolidinedione; Benzyl 2,5-dioxopyrrolid-1-yl Carbonate; Benzyl 2,5-dioxopyrrolidin-1-yl Carbonate; B
• Storage: -20°C
• IUPAC Name: benzyl (2,5-dioxopyrrolidin-1-yl) carbonate
• InChI: InChI=1S/C12H11NO5/c14-10-6-7-11(15)13(10)18-12(16)17-8-9-4-2-1-3-5-9/h1-5H,6-8H2
• InChIKey: MJSHDCCLFGOEIK-UHFFFAOYSA-N
• SMILES: C1CC(=O)N(C1=O)OC(=O)OCC2=CC=CC=C2

N-(N-Benzyloxycarbonyloxy)succinimide（Cat No.:R020958）is a reactive coupling reagent commonly used in peptide synthesis and organic derivatization. It features a benzyloxycarbonyl (Cbz) protecting group linked through a carbamate bond to N-hydroxysuccinimide (NHS), forming an activated ester. This compound facilitates efficient introduction of the Cbz protecting group onto amines under mild conditions, enhancing selectivity and yield. The NHS moiety ensures rapid acylation of nucleophiles, especially in the presence of bases. It is widely used in medicinal chemistry and bioconjugation, where temporary protection of functional groups is crucial during multistep synthetic sequences.