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
Empirical Formula (Hill Notation):
C9H19N2O
CAS Number:
Molecular Weight:
171.26
Beilstein/REAXYS Number:
3933966
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

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.

Packaging

1, 5 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

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)
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)
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...
Jianfei Jiang et al.
The Journal of pharmacology and experimental therapeutics, 320(3), 1050-1060 (2006-12-21)
Suppression of mitochondrial production of reactive oxygen species is a promising strategy against intrinsic apoptosis typical of degenerative diseases. Stable nitroxide radicals such as 4-hydroxy-2,2,6,6-tetramethyl piperidine-1-oxyl (TEMPOL) and its analogs combine several important features, including recycleability, electron acceptance from respiratory...
Articles
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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