What Is tert-Butyl 2,7-Diazabicyclo[4.2.0]octane-2-carboxylate?

tert-Butyl 2,7-diazabicyclo[4.2.0]octane-2-carboxylate (Aladdin SKU B627753) is a bicyclic nitrogen-containing heterocycle in which a six-membered diazinane ring is fused to a four-membered azetidine ring, generating a rigid, conformationally constrained scaffold. The N-2 nitrogen bears a tert-butoxycarbonyl (Boc) protecting group, leaving the N-7 nitrogen available for further synthetic elaboration. This architecture is representative of the strained bicyclic amines that have attracted significant interest in modern drug discovery as bioisosteres and three-dimensional replacements for flat aromatic heterocycles.

The compound is catalogued under internal reference YS:PBN20120023 and is supplied by Aladdin Scientific for use as a research reagent and synthetic building block.

Handling, Storage, and Stability

As with most Boc-protected secondary amines, tert-Butyl 2,7-diazabicyclo[4.2.0]octane-2-carboxylate should be stored in a tightly sealed container under cool, dry conditions and protected from moisture and strong acids. Exposure to strong protic acids (e.g., trifluoroacetic acid or HCl in dioxane) will cleave the Boc group, which is useful synthetically but must be avoided during routine storage.

Researchers are advised to handle the compound under an inert atmosphere when working with solutions, particularly in protic solvents, to minimise adventitious Boc removal or amine oxidation. Specific melting point, logP, and long-term stability data should be confirmed against the current Certificate of Analysis (CoA) provided with each lot.

Synthetic Applications and Role as a Building Block

The primary value of tert-Butyl 2,7-diazabicyclo[4.2.0]octane-2-carboxylate lies in its use as a conformationally restricted diamine building block. The free secondary amine at N-7 can participate in acylation, sulfonylation, reductive amination, and transition-metal-catalysed cross-coupling reactions, enabling rapid diversification of the bicyclic core.

In medicinal chemistry, such bicyclic diamine scaffolds are employed to introduce three-dimensional character into lead compounds, improve selectivity, and modulate pharmacokinetic properties (e.g., aqueous solubility and metabolic stability) relative to monocyclic or flat aromatic analogues. The Boc group at N-2 can be selectively removed under standard acidic conditions to expose a second amine handle for orthogonal functionalisation.

Researchers exploring structure–activity relationships (SAR) in kinase inhibitor, GPCR ligand, or protease inhibitor programmes may find this scaffold particularly useful as a bioisosteric replacement for piperazine or piperidine moieties.

Purity, Specifications, and Quality Assurance

Aladdin Scientific supplies tert-Butyl 2,7-diazabicyclo[4.2.0]octane-2-carboxylate (B627753) as a research-grade reagent. Purity is confirmed by standard analytical methods such as HPLC and NMR; the precise purity specification and analytical data are detailed in the lot-specific Certificate of Analysis (CoA) available upon request or via the Aladdin website.

Researchers requiring material for GMP or clinical use should contact Aladdin Scientific directly to discuss custom specifications. For routine synthetic and screening applications, the research-grade material is appropriate. Lot-to-lot consistency is monitored through internal quality control procedures referenced under YS:PBN20120023.

Ordering and Availability

tert-Butyl 2,7-diazabicyclo[4.2.0]octane-2-carboxylate is available from Aladdin Scientific under SKU B627753. Orders can be placed through the Aladdin online store, by contacting your local Aladdin sales representative, or via authorised distributors. For bulk quantities, custom packaging, or expedited delivery enquiries, please contact Aladdin customer service directly.

When placing an order, please quote SKU B627753 and specify the required quantity and any purity or packaging requirements. A Safety Data Sheet (SDS) and Certificate of Analysis are available for each lot upon request.