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Merck
CN

763284

9-Azabicyclo[3.3.1]nonane N-oxyl

greener alternative

95%, solid

Synonym(s):

9-Azabicyclo[3.3.1]nonane N-oxyl radical, ABNO

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About This Item

Empirical Formula (Hill Notation):
C8H14NO
CAS Number:
31785-68-9
Molecular Weight:
140.20
UNSPSC Code:
12161600
PubChem Substance ID:
329767041
NACRES:
NA.22
Beilstein/REAXYS Number:
1681761

Key Documents

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Product Name

9-Azabicyclo[3.3.1]nonane N-oxyl, 95%

SMILES string

C[C@@]12CCC[C@@](C)(CCC1)N2[O]

InChI key

GGWCZKZSILYISB-AOOOYVTPSA-N

InChI

1S/C10H18NO/c1-9-5-3-7-10(2,11(9)12)8-4-6-9/h3-8H2,1-2H3/t9-,10+

assay

95%

form

solid

reaction suitability

reagent type: ligand

greener alternative product characteristics

Catalysis
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sustainability

Greener Alternative Product

mp

65-70 °C

greener alternative category

, Aligned

storage temp.

2-8°C

Quality Level

200

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Application

9-Azabicyclo[3.3.1]nonane N-oxyl (ABNO) may be employed for the aerobic oxidation of alcohols.
Catalytic oxidant for copper-catalyzed greener oxidation of alcohols under aerobic conditions.

Copper(I)/ABNO-Catalyzed Aerobic Alcohol Oxidation: Alleviating Steric and Electronic Constraints of Cu/TEMPO Catalyst Systems

General description

9-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.
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pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

hcodes

H302,H318

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000519107
0000519107
0000486438
0000486441
0000486438

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Practical Aerobic Alcohol Oxidation with Cu/Nitroxyl and Nitroxyl/NOx Catalyst Systems.
Miles KC and Stahl SS.
Aldrichimica Acta, 48(1), 8-8 (2015)
Masatoshi Shibuya et al.
The Journal of organic chemistry, 74(12), 4619-4622 (2009-05-30)
A practical, three-step synthetic route to 9-azabicyclo[3.3.1]nonane N-oxyl (ABNO, 3), an unhindered, stable class of nitroxyl radical, has been developed. ABNO exhibits a highly active nature compared with TEMPO in the catalytic oxidation of alcohols to their corresponding carbonyl compounds.
Janelle E Steves et al.
Journal of the American Chemical Society, 135(42), 15742-15745 (2013-10-17)
Cu/TEMPO catalyst systems promote efficient aerobic oxidation of sterically unhindered primary alcohols and electronically activated substrates, but they show reduced reactivity with aliphatic and secondary alcohols. Here, we report a catalyst system, consisting of ((MeO)bpy)Cu(I)(OTf) and ABNO ((MeO)bpy = 4,4'-dimethoxy-2,2'-bipyridine;

Articles

TEMPO催化氧化

TEMPO（2,2,6,6-四甲基哌啶氧基或2,2,6,6-四甲基哌啶1-氧基）及其衍生物在有机氧化反应催化剂中可以作为稳定的硝酰基使用。TEMPO由Lebedev和Kazarnovskii于1960年发现，其具有的稳定自由基性质得益于其庞大的取代基团阻碍了自由基与其他分子之间发生反应。

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he Stahl Lab focuses on the development of catalysts and catalytic reactions for selective oxidation of organic molecules, with particular emphasis on aerobic oxidation reactions.

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