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Sigma-Aldrich

4-Hydroxy-TEMPO

95%

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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

Quality Level

200

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

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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.

Signal Word

Danger

Hazard Statements

H302,H318,H373

Hazard Classifications

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

Target Organs

Liver,spleen

WGK

WGK 1

Flash Point(F)

294.8 °F

Flash Point(C)

146 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Journal of Polymer Science. Part B, Polymer Physics, 31, 1885-1885 (1993)
Synlett, 2767-2767 (2006)
Synthesis of polymer-supported TEMPO catalysts and their application in the oxidation of various alcohols.
Tanyeli C and Gumus A.
Tetrahedron Letters, 44(8), 1639-1642 (2003)
Clean and selective oxidation of alcohols catalyzed by ion-supported TEMPO in water.
Qian W, et al.
Tetrahedron, 62(4), 556-562 (2006)
Medical Science Research, 21, 401-401 (1993)
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