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Sigma-Aldrich

4-Hydroxy-TEMPO

95%

Synonym(s):

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

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About This Item

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

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

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

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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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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Articles

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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