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382000

Sigma-Aldrich

4-Carboxy-TEMPO, free radical

97%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H18NO3
CAS Number:
37149-18-1
Molecular Weight:
200.25
Beilstein/REAXYS Number:
3949026
MDL number:
MFCD00134569
UNSPSC Code:
12352000
PubChem Substance ID:
24863856
NACRES:
NA.22

assay

97%

mp

185-189 °C (lit.)

functional group

carboxylic acid

storage temp.

2-8°C

SMILES string

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

InChI

1S/C10H18NO3/c1-9(2)5-7(8(12)13)6-10(3,4)11(9)14/h7H,5-6H2,1-4H3,(H,12,13)

InChI key

CYQGCJQJIOARKD-UHFFFAOYSA-N

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General description

4-Carboxy-TEMPO is a 4-substituted 2,2,6,6-tetramethylpiperidyl-1-oxy (TEMPO) derivative. 4-carboxy-TEMPO immobilized with 3-aminopropylsilane on the mesoporous silica surface comprises heterogeneous catalytic system employed for various oxidation reactions.

Application

4-Carboxy-TEMPO may be employed as catalyst for the oxidation of regenerated cellulose (viscose rayon) to cellouronic acid.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC2285V
BGBC0893V
BGBB2840V
BGBB2840
BGBB1897

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Nitroxide-mediated oxidation of cellulose using TEMPO derivatives: HPSEC and NMR analyses of the oxidized products.
Shibata I and Isogai A.
Cellulose, 10(4), 335-341 (2003)
J L Lamarque et al.
European journal of radiology, 6(1), 48-52 (1986-02-01)
The meglumine salt of TCA, a piperidinyl nitroxide stable free radical derivative, was tested as an NMR contrast enhancer. This report of its use in animals indicates its usefulness in the enhancement of signal intensity of the kidney and bladder.
Kazuyuki Hosokawa et al.
Free radical biology & medicine, 37(7), 946-952 (2004-09-01)
Three water-soluble carboxy nitroxide antioxidants, 5-carboxy-1,1,3,3-tetramethylisoindolin-2-yloxyl, 4-carboxy-2,2,6,6-tetramethylpiperidin-1-yloxyl, and 3-carboxy-2,2,5,5-tetramethylpyrrolidin-1-yloxyl, show significant impact on the postirradiation survival rates of ataxia telangiectasia (A-T) cells compared to normal cells, an assay which represents a model for understanding the impact of ROS damage on
X Yang et al.
Biophysical journal, 71(3), 1587-1595 (1996-09-01)
Electron paramagnetic resonance spectroscopy and gel permeation chromatography were employed to study the molecular diffusion of a number of small nitroxide spin probes (approximately 7-9 A diameter) into the central cavity of the iron-storage protein ferritin. Charge and polarity of
Comparison of two MCM-41 grafted TEMPO catalysts in selective alcohol oxidation.
Brunel D, et al.
Applied Catalysis A: General, 213(1), 73-82 (2001)
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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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