Description

tert-Butyl 3,9-diazabicyclo[4.2.1]nonane-3-carboxylate (CAS No. 286947-16-8) is a highly specialized bicyclic amine derivative with the molecular formula C₁₂H₂₂N₂O₂. This compound features a unique diazabicyclo[4.2.1]nonane core structure, protected by a tert-butoxycarbonyl (Boc) group, making it an invaluable intermediate in organic synthesis and pharmaceutical research. With a purity grade suitable for laboratory and industrial applications, this chemical is rigorously tested to ensure consistency and performance. Ideal for researchers developing novel bioactive compounds, peptidomimetics, or catalysts, it offers excellent reactivity in N-heterocycle functionalization and asymmetric synthesis. Packaged under inert conditions to maintain stability, this product is a must-have for chemists working in medicinal chemistry, drug discovery, and advanced material science.

Properties

• CAS Number: 286947-16-8
• Complexity: 273
• IUPAC Name: tert-butyl 3,9-diazabicyclo[4.2.1]nonane-3-carboxylate
• InChI: InChI=1S/C12H22N2O2/c1-12(2,3)16-11(15)14-7-6-9-4-5-10(8-14)13-9/h9-10,13H,4-8H2,1-3H3
• InChI Key: WFPATFQNPHQQIG-UHFFFAOYSA-N
• Exact Mass: 226.168127949
• Molecular Formula: C12H22N2O2
• Molecular Weight: 226.32
• SMILES: CC(C)(C)OC(=O)N1CCC2CCC(C1)N2
• Topological: 41.6
• Monoisotopic Mass: 226.168127949
• Synonyms: 286947-16-8, tert-butyl 3,9-diazabicyclo[4.2.1]nonane-3-carboxylate, DTXSID20594971, tert-Butyl 3,9-diazabicyclo(4.2.1)nonane-3-carboxylate, DTXCID50545734, 815-560-9, 3-Boc-3,9-diaza-bicyclo[4.2.1]nonane, 3,9-Diazabicyclo[4.2.1]nonane-3-carboxylic acid, 1,1-dimethylethyl ester, cis-tert-Butyl 3,9-diazabicyclo[4.2.1]nonane-3-carboxylate, tert-butyl 4,9-diazabicyclo[4.2.1]nonane-4-carboxylate, SCHEMBL4321473, 3-Tert-butoxycarbonyl-3,9-diazabicyclo-[4.2.1]-nonane, WFPATFQNPHQQIG-UHFFFAOYSA-N, LLA94716, AKOS015950818, PB26916, 3-Boc-3,9-diazabicyclo[4.2.1]nonane, AS-72942, DB-067968, CS-0036882, EN300-89025, W14564, F2147-1738, tert-butyl3,9-diazabicyclo[4.2.1]nonane-3-carboxylate, (+/-)-3-tert-butoxycarbonyl-3,9-diaza-bicyclo[4.2.1]nonane

Application

tert-Butyl 3,9-diazabicyclo[4.2.1]nonane-3-carboxylate serves as a key building block in the synthesis of complex nitrogen-containing heterocycles, particularly in pharmaceutical research. Its Boc-protected amine group allows for selective deprotection, enabling controlled modifications in multi-step reactions. This compound is widely used in the development of enzyme inhibitors, receptor ligands, and other biologically active molecules. Researchers also employ it in the preparation of chiral catalysts for asymmetric transformations. Its rigid bicyclic structure contributes to the stereochemical control of target molecules.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2 (100%)
• STOT SE 3 (100%)

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