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163945

Sigma-Aldrich

4-Amino-TEMPO, free radical

97%

Synonym(s):

4-Amino-2,2,6,6-tetramethylpiperidine-1-oxyl, 4-Amino-2,2,6,6-tetramethylpiperidinyloxy, free radical, 4-Amino-TEMPO

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About This Item

Empirical Formula (Hill Notation):
C9H19N2O
CAS Number:
14691-88-4
Molecular Weight:
171.26
Beilstein:
3933966
EC Number:
238-738-2
MDL number:
MFCD00006479
UNSPSC Code:
12352000
PubChem Substance ID:
24850044
NACRES:
NA.22

Assay

97%

form

solid

mp

~0 °C (lit.)

storage temp.

2-8°C

SMILES string

CC1(C)CC(N)CC(C)(C)N1[O]

InChI

1S/C9H19N2O/c1-8(2)5-7(10)6-9(3,4)11(8)12/h7H,5-6,10H2,1-4H3

InChI key

XUXUHDYTLNCYQQ-UHFFFAOYSA-N

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Application

Useful spin label for studying biological systems, polymers, and as a building block for more elaborate spin labels.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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N Naber et al.
Biochemistry, 33(13), 3855-3861 (1994-04-05)
Each actin molecule contains a nucleotide, tightly bound in a deep cleft that divides the molecule. To probe conformational changes within this region of the molecule, we have incorporated two spin label analogues of ATP into actin. In both analogs
Journal of Colloid and Interface Science, 165, 236-236 (1994)
SEC-MALS analysis of cellouronic acid prepared from regenerated cellulose by TEMPO-mediated oxidation.
Shibata I, et al.
Cellulose, 13(1), 73-80 (2006)
Darja Jaušovec et al.
Carbohydrate polymers, 116, 74-85 (2014-12-03)
The chemo-enzymatic modification of cellulose nanofibers (CNFs) using laccase as biocatalysts and TEMPO or 4-Amino-TEMPO as mediators under mild aqueous conditions (pH 5, 30 °C) has been investigated to introduce surface active aldehyde groups. 4-Amino TEMPO turned out to be
Spin-Labeled Dendrimers in EPR Imaging with Low Molecular Weight Nitroxides.
Alexander T. Yordanov et al.
Angewandte Chemie (International ed. in English), 40(14), 2690-2692 (2001-07-18)
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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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