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176141

Sigma-Aldrich

4-Hydroxy-TEMPO

95%

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C9H18NO2
Numero CAS:
2226-96-2
Peso molecolare:
172.24
Beilstein:
1422990
Numero CE:
218-760-9
Numero MDL:
MFCD00006478
Codice UNSPSC:
12352119
ID PubChem:
24850555
NACRES:
NA.22

Saggio

95%

Stato

solid

Composizione

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

Punto di fusione

69-71 °C (lit.)

Gruppo funzionale

hydroxyl

Temperatura di conservazione

2-8°C

Stringa SMILE

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
UZFMOKQJFYMBGY-UHFFFAOYSA-N

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Descrizione generale

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.

Applicazioni

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.

Avvertenze

Danger

Indicazioni di pericolo

H302,H318,H373

Classi di pericolo

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

Organi bersaglio

Liver,spleen

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 1

Punto d’infiammabilità (°F)

294.8 °F - DIN 51758

Punto d’infiammabilità (°C)

146 °C - DIN 51758

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
BCCF4337
BCCB3715
BCBX3604
0000030304
0000027546

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Sigma-Aldrich

390380

4-Acetamido-TEMPO, free radical

4-Hydroxy-TEMPO-15N 98 atom % 15N, 97% (CP)

Sigma-Aldrich

705748

4-Hydroxy-TEMPO-15N

2,2,6,6-Tetramethyl-4-piperidinol 98%

Sigma-Aldrich

115746

2,2,6,6-Tetramethyl-4-piperidinol

Acrylamide for molecular biology, ≥99% (HPLC)

Sigma-Aldrich

A9099

Acrylamide

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)
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.
Medical Science Research, 21, 401-401 (1993)
Journal of Polymer Science. Part B, Polymer Physics, 31, 1885-1885 (1993)
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Articoli

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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