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:
Molecular Weight:
172.24
UNSPSC Code:
12352119
NACRES:
NA.22
PubChem Substance ID:
EC Number:
218-760-9
Beilstein/REAXYS Number:
1422990
MDL number:
Assay:
95%
Form:
solid
Quality Level
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
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
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
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.
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.
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
hcodes
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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Articles
TEMPO（2,2,6,6-四甲基哌啶氧基或2,2,6,6-四甲基哌啶1-氧基）及其衍生物在有机氧化反应催化剂中可以作为稳定的硝酰基使用。TEMPO由Lebedev和Kazarnovskii于1960年发现，其具有的稳定自由基性质得益于其庞大的取代基团阻碍了自由基与其他分子之间发生反应。
Z Sledziński et al.
International journal of pancreatology : official journal of the International Association of Pancreatology, 18(2), 153-160 (1995-10-01)
Rats develop acute pancreatitis when infused iv for 3 h with cerulein (10 micrograms/kg/h). Autopsies of the pancreas seen by light microscope show interstitial edema, acinar cells vacuolization, and leukocyte margination in pancreatic capillaries; under electron microscope, severe damage concerning
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 176141-1G | 04061835554423 |
| 176141-25G | 04061835521180 |
| 176141-5G | 04061838752758 |