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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

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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
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

65-70 °C

greener alternative category

, Aligned

storage temp.

2-8°C

Quality Level

200

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1 of 4

This Item
701718151076178713
9-Azabicyclo[3.3.1]nonane N-oxyl 95%

Sigma-Aldrich

763284

9-Azabicyclo[3.3.1]nonane N-oxyl

2-Azaadamantane-N-oxyl 90%

Sigma-Aldrich

701718

2-Azaadamantane-N-oxyl

9-Borabicyclo[3.3.1]nonane solution 0.5 M in THF

Sigma-Aldrich

151076

9-Borabicyclo[3.3.1]nonane solution

9-Borabicyclo[3.3.1]nonane dimer

Sigma-Aldrich

178713

9-Borabicyclo[3.3.1]nonane dimer

assay

95%

assay

90%

assay

-

assay

-

reaction suitability

reagent type: ligand

reaction suitability

reagent type: oxidant

reaction suitability

reagent type: reductant

reaction suitability

reagent type: reductant

form

solid

form

powder

form

liquid

form

solid

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

storage temp.

-

mp

65-70 °C

mp

182-189 °C (D)

mp

-

mp

150-152 °C (lit.)

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

greener alternative product characteristics

-

greener alternative product characteristics

-

greener alternative product characteristics

-

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.[1] 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.[2]
We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

Application

9-Azabicyclo[3.3.1]nonane N-oxyl (ABNO) may be employed for the aerobic oxidation of alcohols.[3]
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

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
0000486441

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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.
Practical Aerobic Alcohol Oxidation with Cu/Nitroxyl and Nitroxyl/NOx Catalyst Systems.
Miles KC and Stahl SS.
Aldrichimica Acta, 48(1), 8-8 (2015)
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;

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Stahl Group – Professor Product Portal

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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