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Merck

176141

4-Hydroxy-TEMPO

95%

Synonym(s):

4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl, TEMPOL

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About This Item

Empirical Formula (Hill Notation):
C9H18NO2
CAS Number:
2226-96-2
Molecular Weight:
172.24
UNSPSC Code:
12352119
NACRES:
NA.22
PubChem Substance ID:
24850555
EC Number:
218-760-9
Beilstein/REAXYS Number:
1422990
MDL number:
MFCD00006478
Assay:
95%
Form:
solid

Key Documents

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InChI key

UZFMOKQJFYMBGY-UHFFFAOYSA-N

InChI

1S/C9H18NO2/c1-8(2)5-7(11)6-9(3,4)10(8)12/h7,11H,5-6H2,1-4H3

SMILES string

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

assay

95%

form

solid

composition

Carbon content, 60.6-65.0% , Nitrogen content, 7.8-8.4%

mp

69-71 °C (lit.)

functional group

hydroxyl

storage temp.

2-8°C

Quality Level

200

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Application

Spin label reagent used in the chatacterization of antagonist and agonist binding sites of NK1 receptor. Also used to measure reactive oxygen generation in heart muscle by electron spin resonance spectroscopy. Cells that overexpress CYP2E1 can be protected from arachidonic acid toxicity damage by TEMPOL.
4-Hydroxy-TEMPO (HO-TEMPO) may be employed as catalyst for the oxidation of alcohols to the corresponding aldehydes. It may be employed for the preparation of TEMPO based polymer catalyst systems, which are useful for the Anelli oxidation of various primary alcohols. It may be used as starting reagent in the synthesis of 4-(2,2,6,6-tetramethyl-1-oxyl-4-piperidoxyl)butyl bromide.
A fluorous-tagged TEMPO derivative was prepared from the derived TEMPO propargylic ether and subsequent "click" reaction with a fluorous azide. This TEMPO derivative proved to be a highly effective catalyst in the oxidation of alcohols with bleach.
Spin label for studying biological compounds and polymers.

General description

4-Hydroxy-TEMPO is a 4-substituted 2,2,6,6-tetramethylpiperidyl-1-oxy (TEMPO) derivative. It is a low-molecular weight compound and has been proposed as superoxide dismutase mimic.

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - STOT RE 2 Oral

target_organs

Liver,spleen

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

294.8 °F - DIN 51758

flash_point_c

146 °C - DIN 51758

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000235723
WXBF7096V
BCCK5479
0000131306
0000131307

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Clean and selective oxidation of alcohols catalyzed by ion-supported TEMPO in water.
Qian W, et al.
Tetrahedron, 62(4), 556-562 (2006)
Synthesis of polymer-supported TEMPO catalysts and their application in the oxidation of various alcohols.
Tanyeli C and Gumus A.
Tetrahedron Letters, 44(8), 1639-1642 (2003)
Synlett, 2767-2767 (2006)
Journal of Polymer Science. Part B, Polymer Physics, 31, 1885-1885 (1993)
T Tanigawa et al.
Free radical research communications, 19 Suppl 1, S171-S176 (1993-01-01)
A method was designed to detect free radicals in circulating blood of animals using extracorporeal circulation and electron paramagnetic resonance (EPR). An arterial-venous shunt was inserted into male Wistar rats between the distal abdominal aorta and the inferior vena cava.
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