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763284

Sigma-Aldrich

9-Azabicyclo[3.3.1]nonane N-oxyl

greener alternative

95%

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C8H14NO
Numero CAS:
31785-68-9
Peso molecolare:
140.20
Beilstein:
1681761
Codice UNSPSC:
12161600
ID PubChem:
329767041
NACRES:
NA.22

Saggio

95%

Forma fisica

solid

Impiego in reazioni chimiche

reagent type: ligand

Caratteristiche più verdi

Catalysis
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sustainability

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Punto di fusione

65-70 °C

Categoria alternativa più verde

, Aligned

Temperatura di conservazione

2-8°C

Stringa SMILE

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+
GGWCZKZSILYISB-AOOOYVTPSA-N

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Categorie correlate

Descrizione generale

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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Applicazioni

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

Pittogrammi

CorrosionExclamation mark
GHS05,GHS07

Avvertenze

Danger

Indicazioni di pericolo

H302,H318

Classi di pericolo

Acute Tox. 4 Oral - Eye Dam. 1

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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Certificati d'analisi (COA)

Lot/Batch Number
BGBC3376V
BGBC3133V
MKBL6032

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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;

Articoli

TEMPO Catalyzed Oxidations

TEMPO (2,2,6,6-Tetramethylpiperidinyloxy or 2,2,6,6-Tetramethylpiperidine 1-oxyl) and its derivatives are stable nitroxy radicals used as catalysts in organic oxidation reactions. TEMPO was discovered by Lebedev and Kazarnovskii in 1960. The stable free radical nature of TEMPO is due to the presence of bulky substituent groups, which hinder the reaction of the free radical with other molecules.

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