TEMPO

Name: TEMPO
Brand: ALDRICH

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

UNSPSC Code:

12352119

NACRES:

NA.22

PubChem Substance ID:

24866699

EC Number:

219-888-8

Beilstein/REAXYS Number:

1422418

MDL number:

MFCD00009599

Product Name

TEMPO, purified by sublimation, 99%

InChI key

QYTDEUPAUMOIOP-UHFFFAOYSA-N

InChI

1S/C9H18NO/c1-8(2)6-5-7-9(3,4)10(8)11/h5-7H2,1-4H3

SMILES string

CC1(C)CCCC(C)(C)N1[O]

assay

99%

form

solid

purified by

sublimation

reaction suitability

reagent type: oxidant

Quality Level

200

greener alternative product characteristics

Catalysis
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sustainability

Greener Alternative Product

mp

36-38 °C (lit.)

greener alternative category

Aligned

storage temp.

2-8°C

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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.

General description

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

Features and Benefits

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Green Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

pictograms

GHS05

signalword

Danger

hcodes

H314,H412

pcodes

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

Hazard Classifications

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

Storage Class

8A - Combustible corrosive hazardous materials

wgk

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

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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)

Efficient and stereoselective nitration of mono- and disubstituted olefins with AgNO2 and TEMPO.

Soham Maity et al.

Journal of the American Chemical Society, 135(9), 3355-3358 (2013-02-15)

Nitroolefin is a common and versatile reagent. Its synthesis from olefin is generally limited by the formation of mixture of cis and trans compounds. Here we report that silver nitrite (AgNO2) along with TEMPO can promote the regio- and stereoselective

Cellulose nanowhiskers extracted from TEMPO-oxidized jute fibers.

Xinwang Cao et al.

Carbohydrate polymers, 90(2), 1075-1080 (2012-07-31)

Cellulose nanowhiskers is a kind of renewable and biocompatible nanomaterials evoke much interest because of its versatility in various applications. Here, for the first time, a novel controllable fabrication of cellulose nanowhiskers from jute fibers with a high yield (over

Cu-NHC-TEMPO catalyzed aerobic oxidation of primary alcohols to aldehydes.

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

Mechanism of copper(I)/TEMPO-catalyzed aerobic alcohol oxidation.

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

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