ol

• ChemBase ID: 125436
• Molecular Formular: C9H18NO2
• Molecular Mass: 172.24472
• Monoisotopic Mass: 172.13375382
• SMILES: CC1(C)CC(CC(C)(C)N1[O])O
• Canonical SMILES: OC1CC(C)(C)N(C(C1)(C)C)[O]
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: ol
• IUPAC Traditional name: tyrosine(.)
• Synonyms: Tempol; Tanol; TMPN; 4-Oxypiperidol; Nitroxyl 2; HyTEMPO; 4-Hydroxy-TEMPO; 4-Hydroxy-2,2,6,6-tetramethyl-1-piperidin-1-yloxy, free radical; 4-Hydroxy-TEMPO, free radical; Tempol (4-Hydroxy-TEMPO); 4-Hydroxy-2,2,6,6-tetramethylpiperidine 1-oxyl; 4-Hydroxy-TEMPO; 4-羟基-TEMPO, 自由基; 4-羟基-2,2,6,6-四甲基哌啶-1-氧自由基; 哌啶醇氧化物

Database IDs

• CAS Number: 2226-96-2
• EC Number: 218-760-9
• MDL Number: MFCD00006478
• Beilstein Number: 1422990
• PubChem SID: 162219786; 24880214; 24850555
• PubChem CID: 137994
• CHEMBL: 607023
• Chemspider ID: 121639
• Wikipedia Title: 4-Hydroxy-TEMPO

CALCULATED PROPERTIES

• Acid pKa: 15.137116
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.2226221
• LogD (pH = 7.4): 0.22262208
• Log P: 0.2226221
• Molar Refractivity: 47.1746 cm^3
• Polarizability: 18.922005 Å^3
• Polar Surface Area: 23.47 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: orange crystals
• Melting Point: 69-71 °C(lit.); 69-72 °C; 69-72°C
• Flash Point: 146°C(295°F)

Safety Information

• RTECS: TN8991000
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 22-36/37/38; 22-37/38-41
• Safety Statements: 26-36; 26-36/3/39-60
• TSCA Listed: 是
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335; H318-H315-H302-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P305+P351+P338-P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: Others

Product Information

• Purity: ≥97.0% (CHN); 97%; 98+%
• Grade: purum
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C9H18NO2

DETAILS

Sigma Aldrich - H8258

Application
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.

Sigma Aldrich - 176141

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.1
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.
Packaging
1, 5, 25 g in glass bottle

Sigma Aldrich - 56516

Application
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.
Other Notes
Spin label1,2

REFERENCES

• Reviews: Synthesis and reactions of stable nitroxyl radicals: Synthesis, 190, 401 (1971); Advances in the chemistry of nitroxide spin labels: Chem. Rev., 78, 37 (1978); Recent advances in the chemistry of nitroxides and their applications in spin labelling: J. Sci. Ind. Res., 54, 623 (1995). For a brief feature on derived oxoammonium salts, see: Synlett, 1757 (2003).
• Compare also 4-Acetamido-TEMPO, B23456 and TEMPO, A12733.
• Recommended as a stabilizer (antioxidant) for the protection of unsaturated fatty acids and their derivatives: J. Am. Chem. Soc., 101, 6748 (1979).