9-Azabicyclo[3.3.1]nonane N-oxyl

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9-Azabicyclo[3.3.1]nonane N-oxyl Basic information
Product Name:9-Azabicyclo[3.3.1]nonane N-oxyl
Synonyms:NPPN;9-Azabicyclo[3.3.1]nonane N-oxyl;9-Azabicyclo[3.3.1]nonane N-oxyl 95%;exe-3-methylamino-9-boc -9-azabicyclo[3.3.1]nonane;9-AZABICYCLO[3.3.1]NONANE N-OX;9-Azabicyclo[3.3.1]non-9-yloxy;9-azabicyclo[3.3.1]nonan-9-ol;9-hydroxy-9-azabicyclo[3.3.1]nonane
CAS:31785-68-9
MF:C8H14NO*
MW:140.20286
EINECS:803-697-7
Product Categories:
Mol File:31785-68-9.mol
9-Azabicyclo[3.3.1]nonane N-oxyl Structure
9-Azabicyclo[3.3.1]nonane N-oxyl Chemical Properties
Melting point 65-70°C
storage temp. 2-8°C
form solid
AppearanceBrown to reddish brown Solid
BRN 1681761
InChIInChI=1S/C8H14NO/c10-9-7-3-1-4-8(9)6-2-5-7/h7-8H,1-6H2
InChIKeySZAKAAGHPLUEPM-UHFFFAOYSA-N
SMILESC12N([O])C(CCC1)CCC2 |^1:2|
Safety Information
Hazard Codes Xn
Risk Statements 22-41-52/53
Safety Statements 26-39-61
WGK Germany 3
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Eye Dam. 1
MSDS Information
9-Azabicyclo[3.3.1]nonane N-oxyl Usage And Synthesis
Uses9-Azabicyclo[3.3.1]nonane N-oxyl (ABNO) may be employed for the aerobic oxidation of alcohols.
General Description9-Azabicyclo[3.3.1]nonane N-oxyl (ABNO) belongs to a sterically unhindered and stable class of nitroxyl radicals. It efficiently catalyzes the oxidation of alcohols to afford the corresponding carbonyl compounds. ABNO along with (MeObpy)CuI(OTf) (MeObpy =4,4′-dimethoxy-2,2′-bipyridine) comprises a catalytic system. This catalytic system is useful for the aerobic oxidation of all categories of alcohols.
reaction suitabilityreagent type: ligand
Synthesis1. 9-Benzyl-9-azabicyclononan-3-one is reduced to 9-benzyl-9-azabicyclononane in a continuous reactor at 215C with KOH/hydrazine hydrate/ethanol.
2. The product from step 1 is hydrogenated in methanol with Pd/C to remove the benzyl group, yielding 9-azabicyclononane.
3. The product from step 2 is oxidized with urea peroxide catalyzed by sodium tungstate to give the N-oxyl radical.
9-Azabicyclo[3.3.1]nonane N-oxyl Preparation Products And Raw materials
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