Benzyl (1-Benzyl-2,5-Dioxopyrrolidin-3-yl)carbamate: FAQ
Benzyl (1-Benzyl-2,5-Dioxopyrrolidin-3-yl)carbamate: FAQ
Benzyl (1-benzyl-2,5-dioxopyrrolidin-3-yl)carbamate is a succinimide-based, Cbz-protected amino building block used in organic synthesis and medicinal chemistry research, available from Aladdin Scientific as SKU B731068.
- Product Name
- Benzyl (1-benzyl-2,5-dioxopyrrolidin-3-yl)carbamate
- SKU
- B731068
- Core Structural Features
- Succinimide (pyrrolidine-2,5-dione) ring with N-benzyl substitution; Cbz (benzyloxycarbonyl) carbamate protecting group on C-3 amine
- Primary Application
- Building block for organic synthesis, medicinal chemistry, and pharmaceutical research
- Protecting Group
- Cbz (benzyloxycarbonyl), removable by hydrogenolysis
- Supplier
- Aladdin Scientific
Chemical Identity and Structure
Benzyl (1-benzyl-2,5-dioxopyrrolidin-3-yl)carbamate (Aladdin SKU: B731068) is an organic compound featuring two distinct functional motifs. The core is a pyrrolidine-2,5-dione (succinimide) ring bearing an N-benzyl group, making it an N-benzylsuccinimide scaffold. At the C-3 position of the ring, the amine substituent is protected as a benzyloxycarbonyl (Cbz) carbamate.
This dual-benzyl architecture — one benzyl on the succinimide nitrogen and one as the Cbz carbamate ester — makes the compound a bifunctionally differentiated building block. The Cbz group is one of the most widely employed amine protecting groups in synthetic organic and medicinal chemistry, valued for its stability under basic and mildly acidic conditions and its clean removal by catalytic hydrogenolysis.
Handling, Storage, and Safety
As with most synthetic organic reagents, Benzyl (1-benzyl-2,5-dioxopyrrolidin-3-yl)carbamate should be handled following standard laboratory safety practices. Use appropriate personal protective equipment (PPE), including gloves, lab coat, and safety eyewear. Work in a well-ventilated area or fume hood when weighing or dissolving the compound.
For storage, keep the material in a tightly sealed container, protected from moisture and light, at the temperature specified on the product certificate of analysis. Proper storage conditions help maintain reagent integrity and purity over the product's stated shelf life. Always consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for specific hazard classifications, first-aid measures, and disposal guidelines before use.
Note: Specific GHS hazard classifications, recommended storage temperature, and shelf-life data for B731068 should be confirmed in the current product SDS and certificate of analysis available on the Aladdin Scientific website.
Research Applications and Use Cases
Benzyl (1-benzyl-2,5-dioxopyrrolidin-3-yl)carbamate serves as a versatile intermediate in organic synthesis. Its value arises from the combination of a reactive succinimide carbonyl framework with an orthogonally removable Cbz-protected amine at C-3, enabling sequential deprotection and functionalization strategies.
Typical research applications include:
- Medicinal chemistry: Assembly of pyrrolidinedione-containing pharmacophores and peptidomimetic scaffolds relevant to drug discovery programs.
- Total synthesis: Incorporation as a chiral or prochiral building block in multi-step synthesis routes where selective amine deprotection is required.
- Library synthesis: Generation of compound libraries via parallel synthesis, exploiting the dual handles (succinimide carbonyl and Cbz amine) for diversification.
- Chemical biology: Preparation of probe molecules or linker units for bioconjugation applications.
Note: Specific published synthetic procedures citing this exact compound should be verified in the primary literature. Researchers are encouraged to consult current literature for validated protocols.
Ordering, Availability, and Quality
Benzyl (1-benzyl-2,5-dioxopyrrolidin-3-yl)carbamate is available from Aladdin Scientific under SKU B731068. To place an order, visit the Aladdin Scientific website, search by product name or SKU, and proceed through the standard ordering workflow. Registered account holders can access pricing, request quotes, and track orders directly through their account dashboard.
For questions about stock availability, custom pack sizes, bulk quantities, or purity specifications, contact Aladdin Scientific customer service or your regional sales representative. Certificate of Analysis (CoA) documents for specific lot numbers can be requested via the website or customer support channels.
Aladdin Scientific is committed to supplying research-grade reagents with documented purity. Always verify the purity grade and specification on the CoA before use in critical experiments.
Frequently asked questions
What is the chemical structure of Benzyl (1-benzyl-2,5-dioxopyrrolidin-3-yl)carbamate?
The compound consists of a succinimide (pyrrolidine-2,5-dione) ring with a benzyl group on the ring nitrogen (N-1) and a Cbz (benzyloxycarbonyl) carbamate protecting group on the amine at the C-3 position. This gives the molecule two benzyl-containing moieties serving different roles: one as an N-substituent on the succinimide and one as the Cbz ester.
How is the Cbz protecting group removed from this compound?
The Cbz (benzyloxycarbonyl) group is typically removed by catalytic hydrogenolysis, commonly using hydrogen gas over a palladium catalyst (e.g., Pd/C) in a protic solvent such as methanol or ethanol. This cleaves the benzylic C–O bond to liberate the free amine along with toluene and carbon dioxide as byproducts. Researchers should note that the N-benzyl group on the succinimide ring may also be susceptible to hydrogenolysis under these conditions; reaction selectivity should be carefully optimized.
What solvents are suitable for dissolving Benzyl (1-benzyl-2,5-dioxopyrrolidin-3-yl)carbamate?
Based on the compound's structural features — an aromatic-rich, moderately polar organic molecule — common organic solvents such as dichloromethane (DCM), dimethyl sulfoxide (DMSO), dimethylformamide (DMF), ethyl acetate, and tetrahydrofuran (THF) are expected to provide good solubility. The compound is not expected to be appreciably soluble in water. Researchers should perform solubility testing at the required concentration before use in assays or reactions.
What purity grade is Aladdin's B731068, and how can I obtain the Certificate of Analysis?
Aladdin Scientific supplies B731068 as a research-grade reagent. The specific purity value and analytical data (e.g., HPLC, NMR) for each production lot are documented in the Certificate of Analysis (CoA). You can request the CoA for your specific lot number through the Aladdin Scientific website product page or by contacting customer service directly.
Is Benzyl (1-benzyl-2,5-dioxopyrrolidin-3-yl)carbamate available in bulk or custom quantities?
For bulk quantities, custom pack sizes, or special purity requirements beyond standard catalog offerings, please contact Aladdin Scientific customer service or your regional sales representative. They can advise on availability, lead times, and pricing for non-standard quantities.
References
- Wuts, P. G. M.; Greene, T. W. Greene's Protective Groups in Organic Synthesis, 4th ed.; Wiley-Interscience: Hoboken, NJ, 2007. (General reference for Cbz protecting group chemistry.)
- Aladdin Scientific Product Page: Benzyl (1-benzyl-2,5-dioxopyrrolidin-3-yl)carbamate, SKU B731068. Aladdin Scientific Corp.
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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