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Sigma-Aldrich

4-Acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl

greener alternative

purum, ≥98.0% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C11H21N2O2
CAS Number:
Molecular Weight:
213.30
Beilstein:
3546225
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

grade

purum

Quality Level

Assay

≥98.0% (HPLC)

greener alternative product score

old score: 9
new score: 8
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greener alternative product characteristics

Waste Prevention
Safer Solvents and Auxiliaries
Inherently Safer Chemistry for Accident Prevention
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

143-145 °C (lit.)
143-146 °C

greener alternative category

storage temp.

2-8°C

SMILES string

CC(=O)NC1CC(C)(C)N([O])C(C)(C)C1

InChI

1S/C11H21N2O2/c1-8(14)12-9-6-10(2,3)13(15)11(4,5)7-9/h9H,6-7H2,1-5H3,(H,12,14)

InChI key

UXBLSWOMIHTQPH-UHFFFAOYSA-N

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General description

4-Acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl undergoes one-electron oxidation and reduction reactions. Reaction products were analyzed by 1H, 13C and 15N NMR spectral data.
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Application

4-Acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl radical may be employed in the catalytic system used for the regioselective oxidation of curdlan. It may be employed as model nitroxyl radical to study its reaction with thiophosgene. Reaction afforded 2,2,6,6-tetramethylpiperidine and 2,2,6,6-tetramethyl-1-hydroxypiperidine as major products.

Other Notes

New oxidant for the mild oxidation of alcohols to carbonyls

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Reaction of Nitroxides with Sulfur Containing Compounds II [1]. Preparation of Nitroxides Bearing an Isothiocyanate Substituent in View of the Nitroxyl Group Reduction with Thiophosgene.
Zakrzewski J, et al.
Monatshefte fur Chemie / Chemical Monthly, 134(6), 843-850 (2003)
Z. Ma et al.
The Journal of Organic Chemistry, 56, 6110-6110 (1991)
A 1H, 13C and 15N NMR study of oxidation and reduction products of 4-acetamido-2, 2, 6, 6-tetramethylpiperidine-1-oxyl.
Schilf W, et al.
Journal of Molecular Structure, 407(1), 1-3 (1997)
D Metodiewa et al.
Biochemistry and molecular biology international, 40(6), 1211-1219 (1996-12-01)
Two novel 2,2,6,6-tetramethylpiperidine derivatives (Tempace and Troxyl) were synthesized and their capacity to act as scavengers of superoxide, inhibitors of iron and ascorbate-driven Fenton reaction and radioprotectors was tested. The possibility for one-electron oxidation of novel compounds by heme-ferryl species
D Metodiewa et al.
Biochemistry and molecular biology international, 42(6), 1261-1270 (1997-09-26)
A novel complex, Rutoxyl [rutin/4-acetamide-1-hydroxy-2,2,6,6-tetramethylpiperidinium] was synthesized and its structure and anticancer activity were investigated. The results reported here are consistent with our idea, that the formation of such a complex of two biologically active molecules: polyphenolic flavonoid antioxidant (Rutin)

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