176141

4-Hydroxy-TEMPO

95%

• Synonym(e): 4-Hydroxy-2,2,6,6-tetramethyl-piperidin-1-oxyl, TEMPOL
• Empirische Formel (Hill-System): C₉H₁₈NO₂
• CAS-Nummer: 2226-96-2
• Molekulargewicht: 172.24
• Beilstein: 1422990
• EG-Nummer: 218-760-9
• MDL-Nummer: MFCD00006478
• UNSPSC-Code: 12352119
• PubChem Substanz-ID: 24850555
• NACRES: NA.22

Eigenschaften

• Qualitätsniveau: 200
• Assay: 95%
• Form: solid
• Zusammensetzung: Carbon content, 60.6-65.0% ; Nitrogen content, 7.8-8.4%
• mp (Schmelzpunkt): 69-71 °C (lit.)
• Funktionelle Gruppe: hydroxyl
• Lagertemp.: 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
• InChIKey: UZFMOKQJFYMBGY-UHFFFAOYSA-N

Beschreibung

Allgemeine Beschreibung

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.

Anwendung

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.

Sicherheitshinweise

• Piktogramme: GHS08,GHS05,GHS07
• Signalwort: Danger
• H-Sätze: H302,H318,H373
• P-Sätze: P260 - P264 - P280 - P301 + P312 - P305 + P351 + P338 - P314
• Gefahreneinstufungen: Acute Tox. 4 Oral - Eye Dam. 1 - STOT RE 2 Oral
• Zielorgane: Liver,spleen
• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 1
• Flammpunkt (°F): 294.8 °F - DIN 51758
• Flammpunkt (°C): 146 °C - DIN 51758
• Persönliche Schutzausrüstung: dust mask type N95 (US), Eyeshields, Gloves