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426369

Sigma-Aldrich

TEMPO

purified by sublimation, 99%

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:
24866699
NACRES:
NA.22

Assay

99%

form

solid

purified by

sublimation

reaction suitability

reagent type: oxidant

mp

36-38 °C (lit.)

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

For a synthetic protocol using NMP initiators, contributed by Prof. Karen Wooley, please visit our technology spotlight.

Application

Stable nitroxide radical useful in controlling living polymerizations
TEMPO (2,2,6,6-Tetramethyl-1-piperidinyloxy) was used for trapping the styrenyl radical generated from benzoyl peroxide during nitroxide-mediated radical polymerization of styrene. TEMPO-mediated oxidation was employed for the carboxylation of water-resistant nanofibrillated cellulose (NFC) films.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314,H412

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

Certificates of Analysis (COA)

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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
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
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
Xiaolong Liu et al.
The Journal of organic chemistry, 78(17), 8531-8536 (2013-08-16)
Imidazolium salts bearing TEMPO groups react with commercially available copper powder affording Cu-NHC complexes. The in situ generated Cu-NHC-TEMPO complexes are quite efficient catalysts for aerobic oxidation of primary alcohols into aldehydes. The catalyst is easily available, and various primary
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Block Copolymer Synthesis Using a Nitroxide-mediated Radical Polymerization (NMP) Approach

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

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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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