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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:
14691-89-5
Molecular Weight:
213.30
Beilstein:
3546225
EC Number:
423-840-3
MDL number:
MFCD00043593
UNSPSC Code:
12352005
PubChem Substance ID:
329747053
NACRES:
NA.22

grade

purum

Quality Level

200

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

, Re-engineered

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.
We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Waste Prevention”, “Safer Solvents and Auxiliaries” and “Inherently Safer Chemistry for Accident Prevention”. Click here to view its DOZN scorecard.

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
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ9811
BCBR6087V
BCBM2377V
BGBC2293V
BCBK9096V

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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)
A Koceva-Chyła et al.
Anticancer research, 20(6B), 4611-4618 (2001-02-24)
The novel nitroxyl, Tempicol-3 (nitroxide-N-oxide) was synthesized and its capacity to act as a scavenger of hydroxyl radicals was tested. The concentration-dependent reducibility of this novel compound was also examined and compared with those of previously characterized nitroxides, Tempo and
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)
Z. Ma et al.
The Journal of Organic Chemistry, 56, 6110-6110 (1991)
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
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