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176141

Sigma-Aldrich

4-Hydroxy-TEMPO

95%

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Synonym(s):
4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl, TEMPOL
Empirical Formula (Hill Notation):
C9H18NO2
CAS Number:
Molecular Weight:
172.24
Beilstein/REAXYS Number:
1422990
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

form

solid

composition

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

mp

69-71 °C (lit.)

storage temp.

2-8°C

SMILES string

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

InChI

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

InChI key

UZFMOKQJFYMBGY-UHFFFAOYSA-N

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1 of 4

This Item
390380487686371343
4-Hydroxy-TEMPO 95%

176141

4-Hydroxy-TEMPO

4-Acetamido-TEMPO, free radical 97%

390380

4-Acetamido-TEMPO, free radical

4-Hydroxy-TEMPO-d17 97 atom % D, 95% (CP)

487686

4-Hydroxy-TEMPO-d17

Quality Level

200

Quality Level

-

Quality Level

-

Quality Level

-

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

-

mp

69-71 °C (lit.)

mp

143-145 °C (lit.)

mp

69-71 °C (lit.)

mp

99-101 °C (lit.)

form

solid

form

powder

form

solid

form

solid

composition

Carbon content, 60.6-65.0%

composition

-

composition

-

composition

-

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.

Application

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.
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.

signalword

Danger

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

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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T Tanigawa et al.
Free radical research communications, 19 Suppl 1, S171-S176 (1993-01-01)
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Z Sledziński et al.
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Medical Science Research, 21, 401-401 (1993)
Technical production of aldehydes by continuous bleach oxidation of alcohols catalyzed by 4-hydroxy-TEMPO.
Fritz-Langhals E.
Organic Process Research & Development, 9(5), 577-582 (2005)
Journal of Polymer Science. Part B, Polymer Physics, 31, 1885-1885 (1993)

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