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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:
Molecular Weight:
156.25
Beilstein/REAXYS Number:
1422418
EC Number:
MDL number:
UNSPSC Code:
12352119
PubChem Substance ID:
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

signalword

Danger

hcodes

Hazard Classifications

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

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

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


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)
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
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
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

Articles

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

Micro review of reversible addition/fragmentation chain transfer (RAFT) polymerization.

Protocols

We presents an article featuring procedures that describe polymerization of methyl methacrylate and vinyl acetate homopolymers and a block copolymer as performed by researchers at CSIRO.

We present an article about RAFT, or Reversible Addition/Fragmentation Chain Transfer, which is a form of living radical polymerization.

Polymerization via ATRP procedures demonstrated by Prof. Dave Haddleton's research group at the University of Warwick.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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