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214000

Sigma-Aldrich

TEMPO

greener alternative

98%

Synonyma:

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

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About This Item

Empirický vzorec (Hillův zápis):
C9H18NO
Číslo CAS:
2564-83-2
Molekulová hmotnost:
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

Osvědčení o analýze (COA)

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2,2,6,6-Tetramethylpiperidine ≥99%

Sigma-Aldrich

115754

2,2,6,6-Tetramethylpiperidine

TEMPOL A stable, cell-permeable nitroxide that acts as a free radical scavenger and nitric oxide spin trap.

Sigma-Aldrich

581500

TEMPOL

MitoTEMPO ≥98% (HPLC)

Sigma-Aldrich

SML0737

MitoTEMPO

2,2,6,6-Tetramethyl-4-piperidinol 98%

Sigma-Aldrich

115746

2,2,6,6-Tetramethyl-4-piperidinol

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.
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
Jessica M Hoover et al.
Journal of the American Chemical Society, 135(6), 2357-2367 (2013-01-16)
Homogeneous Cu/TEMPO catalyst systems (TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) have emerged as some of the most versatile and practical catalysts for aerobic alcohol oxidation. Recently, we disclosed a (bpy)Cu(I)/TEMPO/NMI catalyst system (NMI = N-methylimidazole) that exhibits fast rates and high selectivities, even
Akira Isogai et al.
Nanoscale, 3(1), 71-85 (2010-10-20)
Native wood celluloses can be converted to individual nanofibers 3-4 nm wide that are at least several microns in length, i.e. with aspect ratios>100, by TEMPO (2,2,6,6-tetramethylpiperidine-1-oxyl radical)-mediated oxidation and successive mild disintegration in water. Preparation methods and fundamental characteristics
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Stahl Group – Professor Product Portal

he Stahl Lab focuses on the development of catalysts and catalytic reactions for selective oxidation of organic molecules, with particular emphasis on aerobic oxidation reactions.

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