Merck
CN
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214000

Sigma-Aldrich

TEMPO

greener alternative

98%

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Synonym(s):
2,2,6,6-Tetramethylpiperidine 1-oxyl, 2,2,6,6-Tetramethyl-1-piperidinyloxy, free radical, TEMPO
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

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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1 of 4

This Item
426369176141581500
TEMPO 98%

Sigma-Aldrich

214000

TEMPO

TEMPO purified by sublimation, 99%

Sigma-Aldrich

426369

TEMPO

4-Hydroxy-TEMPO 95%

Sigma-Aldrich

176141

4-Hydroxy-TEMPO

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

Sigma-Aldrich

581500

TEMPOL

form

solid

form

solid

form

solid

form

crystals, powder

reaction suitability

reagent type: oxidant

reaction suitability

reagent type: oxidant

reaction suitability

-

reaction suitability

-

mp

36-38 °C (lit.)

mp

36-38 °C (lit.)

mp

69-71 °C (lit.)

mp

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

Quality Level

200

Quality Level

-

Quality Level

-

Quality Level

100

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

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 2

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

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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

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.
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)
Hayaka Fukuzumi et al.
Carbohydrate polymers, 93(1), 172-177 (2013-03-08)
Various mechanical disintegration conditions in water were applied to 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO)-oxidized cellulose to prepare TEMPO-oxidized cellulose nanofibrils (TOCNs) of uniform widths ∼4 nm but with three different average lengths, 200, 680, and 1100 nm. The viscosity average degrees of polymerization

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