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Sigma-Aldrich

4-Hydroxy-TEMPO

95%

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C9H18NO2
Número de CAS:
2226-96-2
Peso molecular:
172.24
Beilstein:
1422990
Número CE:
218-760-9
Número MDL:
MFCD00006478
Código UNSPSC:
12352119
ID de la sustancia en PubChem:
24850555
NACRES:
NA.22
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Nivel de calidad

200

Ensayo

95%

Formulario

solid

composición

Carbon content, 60.6-65.0%
Nitrogen content, 7.8-8.4%

mp

69-71 °C (lit.)

grupo funcional

hydroxyl

temp. de almacenamiento

2-8°C

cadena SMILES

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

Clave InChI

UZFMOKQJFYMBGY-UHFFFAOYSA-N

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Descripción general

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.[1]

Aplicación

4-Hydroxy-TEMPO (HO-TEMPO) may be employed as catalyst for the oxidation of alcohols to the corresponding aldehydes.[2] It may be employed for the preparation of TEMPO based polymer catalyst systems, which are useful for the Anelli oxidation of various primary alcohols.[3] It may be used as starting reagent in the synthesis of 4-(2,2,6,6-tetramethyl-1-oxyl-4-piperidoxyl)butyl bromide.[4]
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.[5]
Spin label for studying biological compounds[6][7] and polymers.[8]
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.

Palabra de señalización

Danger

Frases de peligro

H302,H318,H373

Clasificaciones de peligro

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

Órganos de actuación

Liver,spleen

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 1

Punto de inflamabilidad (°F)

294.8 °F - DIN 51758

Punto de inflamabilidad (°C)

146 °C - DIN 51758

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
BCCK5479
0000131307
0000131306
BCCF4337
0000094224

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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
Medical Science Research, 21, 401-401 (1993)
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.
Journal of Polymer Science. Part B, Polymer Physics, 31, 1885-1885 (1993)
Clean and selective oxidation of alcohols catalyzed by ion-supported TEMPO in water.
Qian W, et al.
Tetrahedron, 62(4), 556-562 (2006)
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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