176141

4-Hydroxy-TEMPO

95%

• Synonym(s): 4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl, TEMPOL
• Empirical Formula (Hill Notation): C₉H₁₈NO₂
• CAS Number: 2226-96-2
• Molecular Weight: 172.24
• Beilstein: 1422990
• EC Number: 218-760-9
• MDL number: MFCD00006478
• UNSPSC Code: 12352119
• PubChem Substance ID: 24850555
• NACRES: NA.22

Properties

• 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

Description

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.

Safety Information

• Pictograms: GHS08,GHS05,GHS07
• Signal Word: Danger
• Hazard Statements: H302,H318,H373
• Precautionary Statements: P260 - P264 - P280 - P301 + P312 - P305 + P351 + P338 - P314
• Hazard Classifications: Acute Tox. 4 Oral - Eye Dam. 1 - STOT RE 2 Oral
• Target Organs: Liver,spleen
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1
• Flash Point(F): 294.8 °F - DIN 51758
• Flash Point(C): 146 °C - DIN 51758
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves