MilliporeSigma
All Photos(4)

214000

Sigma-Aldrich

TEMPO

greener alternative

98%

Synonym(s):
TEMPO, 2,2,6,6-Tetramethylpiperidine 1-oxyl, 2,2,6,6-Tetramethyl-1-piperidinyloxy, free radical
Empirical Formula (Hill Notation):
C9H18NO
CAS Number:
Molecular Weight:
156.25
Beilstein:
1422418
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

assay

98%

form

solid

reaction suitability

reagent type: oxidant

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

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

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

Packaging

1, 5, 25 g in glass bottle

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Storage Class Code

8A - Combustible, corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

152.6 °F - closed cup

Flash Point(C)

67 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

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Geisslmeir, David; et al.
Monatshefte fur Chemie / Chemical Monthly, 136(9), 1591-1599 (2005)
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)
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.

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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