tert-Butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Name: tert-Butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
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CAS No. 198989-07-0
Cat. No. CS-0042643
Purity≥97%
MDL No.MFCD06411671

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tert-Butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate|CS-0042643

Structure of 198989-07-0

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General Information

CAS No. 198989-07-0
Cat. No. CS-0042643
Purity ≥97%
MDL No. MFCD06411671
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₈N₂O₂
Molecular Weight 198.26
Synonym(s) (-)-2-(tert-butoxycarbonyl)-(1R,4R)-2,5-diaza-bicyclo[2.2.1]heptane
SMILES O=C(N1C[C@@H]2NC[C@H]1C2)OC(C)(C)C

Description

tert-Butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate features a rigid bicyclic scaffold with two nitrogen atoms at the bridgehead positions, delivering enhanced basicity and structural preorganization. This bench-stable derivative enables efficient incorporation into catalytic systems and asymmetric synthesis workflows, where its defined geometry supports high stereocontrol in C–H functionalization and transition-metal-catalyzed transformations.

Application

tert-Butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate serves as a robust, bench-stable scaffold for constructing nitrogen-rich heterocycles. Its rigid bicyclic core enables precise stereochemical control in medicinal chemistry applications, while the tert-butyl ester facilitates straightforward deprotection under mild acidic conditions. The molecule exhibits excellent functional group tolerance and functions effectively in coupling reactions, enabling efficient access to complex alkaloid frameworks and catalytic intermediates.

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 41.57
LogP 0.9676
H_Acceptors 3
H_Donors 1
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aliphatic heterocycle compounds Pyrrolidine compounds

Building Blocks Skeleton Aliphatic heterocycle compounds Piperazine compounds

Building Blocks Skeleton Bridge Rings compounds Other bridge ring compounds

Key Words

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tert-Butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

CAS No. 198989-07-0

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