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214000

Sigma-Aldrich

TEMPO

greener alternative

98%

Sinónimos:

2,2,6,6-Tetramethylpiperidine 1-oxyl, 2,2,6,6-Tetramethyl-1-piperidinyloxy, free radical, TEMPO

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About This Item

Fórmula empírica (notación de Hill):
C9H18NO
Número de CAS:
2564-83-2
Peso molecular:
156.25
Beilstein/REAXYS Number:
1422418
EC Number:
219-888-8
MDL number:
MFCD00009599
UNSPSC Code:
12352119
PubChem Substance ID:
24852819
NACRES:
NA.22

Quality Level

200

assay

98%

form

solid

reaction suitability

reagent type: oxidant

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

36-38 °C (lit.)

greener alternative category

Aligned,

storage temp.

2-8°C

SMILES string

CC1(C)CCCC(C)(C)N1[O]

InChI

1S/C9H18NO/c1-8(2)6-5-7-9(3,4)10(8)11/h5-7H2,1-4H3

InChI key

QYTDEUPAUMOIOP-UHFFFAOYSA-N

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General description

TEMPO (2,2,6,6-Tetramethylpiperidin-1-oxyl) is a stable free radical commonly used as an oxidizing agent in organic synthesis. Copper/TEMPO has been utilized in the catalytic oxidation of primary alcohols to aldehydes.
We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Find details here.

Application

TEMPO can be used:
  • As a catalytic oxidant for copper-catalyzed, greener oxidation of alcohols under aerobic conditions.
  • As a catalytic oxidant in the iodobenzene diacetae oxidation of nerol to neral.
  • For trapping the styrenyl radical generated from benzoyl peroxide during nitroxide-mediated radical polymerization of styrene.
  • In the carboxylation of water-resistant nanofibrillated cellulose (NFC) films.

Copper(I)/TEMPO-catalyzed aerobic oxidation of primary alcohols to aldehydes with ambient air

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314,H412

Hazard Classifications

Aquatic Chronic 3 - Eye Dam. 1 - Skin Corr. 1C

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 2

flash_point_f

152.6 °F - closed cup

flash_point_c

67 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Visite la Librería de documentos

Geisslmeir, David; et al.
Monatshefte fur Chemie / Chemical Monthly, 136(9), 1591-1599 (2005)
Wan Ru Leow et al.
Science (New York, N.Y.), 368(6496), 1228-1233 (2020-06-13)
Chemicals manufacturing consumes large amounts of energy and is responsible for a substantial portion of global carbon emissions. Electrochemical systems that produce the desired compounds by using renewable electricity offer a route to lower carbon emissions in the chemicals sector.
Block copolymer synthesis using a commercially available nitroxide-mediated radical polymerization (NMP) initiator.
Lee NS and Wooley KL.
Material Matters, 5, 8-15 (2010)
Solvent effect on (2, 2, 6, 6-Tetramethylpiperidine-1-yl) oxyl (TEMPO): a RISM-SCF-SEDD study.
Fernandez MJF and Sato H.
Theoretical Chemistry Accounts, 130(2-3), 299-304 (2011)
Paula Navalpotro et al.
Advanced science (Weinheim, Baden-Wurttemberg, Germany), 5(10), 1800576-1800576 (2018-10-26)
Aqueous biphasic systems (ABS) formed by water, ionic liquids (ILs), and salts, in which the two phases are water rich, are demonstrated here to act as potential membrane-free batteries. This concept is feasible due to the selective enrichment of redox
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