Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

763284

Sigma-Aldrich

9-Azabicyclo[3.3.1]nonane N-oxyl

greener alternative

95%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

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

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

SMILES string

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

InChI

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

InChI key

GGWCZKZSILYISB-AOOOYVTPSA-N

Looking for similar products? Visit Product Comparison Guide

Related Categories

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.
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.
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

Signal Word

Danger

Hazard Statements

H302,H318

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000281845
0000184521
BGBC3376V
BGBC3133V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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;

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service