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390380

Sigma-Aldrich

4-Acetamido-TEMPO, free radical

97%

Synonym(s):

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

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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:
12352000
PubChem Substance ID:
24864140
NACRES:
NA.22

Assay

97%

form

powder

mp

143-145 °C (lit.)

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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Application

Oxidizes alcohols to carbonyl compounds in the presence of TsOH.

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

Certificates of Analysis (COA)

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Erika Watanabe et al.
Carbohydrate polymers, 100, 74-79 (2013-11-06)
Pure (1→3)-β-polyglucuronic acid sodium salt was prepared from curdlan by oxidation with 4-acetamido-TEMPO/NaClO/NaClO₂ in water at pH 4.7 and 35°C. The oxidation conditions, including the reaction time and amounts of reagents added, were optimized for the preparation of (1→3)-β-polyglucuronic acids
Oxidation of vic-Diols to α-dicarbonyl compounds using the oxoammonium salt derived from 4-acetamido-TEMPO and p-toluenesulfonic acid.
Banwell MG, et al.
The Journal of Organic Chemistry, 59(21), 6338-6343 (1994)
Lenka Vítková et al.
Polymers, 11(9) (2019-09-22)
In the current study, we present methods of sodium hyaluronate, also denoted as hyaluronan (HA), nanofiber fabrication using a direct-current (DC) electric field. HA was spun in combination with poly(vinyl alcohol) (PVA) and polyethylene oxide (PEO) and as a pure
The Journal of Organic Chemistry, 56, 6110-6110 (1991)
Iron Chloride/4-Acetamido-TEMPO/Sodium Nitrite-Catalyzed Aerobic Oxidation of Primary Alcohols to the Aldehydes.
Yin W, et al.
Advanced Synthesis & Catalysis, 352(1, 113-118 (2010)
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Articles

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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