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TEMPO

Name: TEMPO
Brand: ALDRICH

98%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₉H₁₈NO

CAS Number:

2564-83-2

Molecular Weight:

156.25

Beilstein:

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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Oxidation Reagents

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.

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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

GHS05

Signal Word

Danger

Hazard Statements

H314,H412

Precautionary Statements

P260 - P273 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338

Hazard Classifications

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

WGK

WGK 2

Flash Point(F)

closed cup

Flash Point(C)

closed cup

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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Geisslmeir, David; et al.

Monatshefte fur Chemie / Chemical Monthly, 136(9), 1591-1599 (2005)

Chloride-mediated selective electrosynthesis of ethylene and propylene oxides at high current density.

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.

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)

Block copolymer synthesis using a commercially available nitroxide-mediated radical polymerization (NMP) initiator.

Lee NS and Wooley KL.

Material Matters, 5, 8-15 (2010)

Pioneering Use of Ionic Liquid-Based Aqueous Biphasic Systems as Membrane-Free Batteries.

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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