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426369

Sigma-Aldrich

TEMPO

purified by sublimation, 99%

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:
NACRES:
NA.22

Quality Level

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

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.
Stable nitroxide radical useful in controlling living polymerizations

Packaging

1, 5 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).

Block copolymer synthesis using a commercially available nitroxide-mediated radical polymerization (NMP) initiator.
Lee NS and Wooley KL.
Material Matters, 5, 8-15 (2010)
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
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
David I Pattison et al.
Free radical biology & medicine, 53(9), 1664-1674 (2012-09-15)
Protein oxidation occurs during multiple human pathologies, and protein radicals are known to induce damage to other cell components. Such damage may be modulated by agents that scavenge protein radicals. In this study, the potential protective reactions of the nitroxide
Enantioselective synthesis of epoxides having a tetrasubstituted trifluoromethylated carbon center: methylhydrazine-induced aerobic epoxidation of β,β-disubstituted enones.
Hiroyuki Kawai et al.
Angewandte Chemie (International ed. in English), 52(8), 2221-2225 (2013-01-23)

Articles

Block Copolymer Synthesis Using a Nitroxide-mediated Radical Polymerization (NMP) Approach

A detailed article on block copolymer synthesis using a nitroxide-mediated radical polymerization (NMP) approach.

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

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

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.

A Micro Review of Reversible Addition/Fragmentation Chain Transfer (RAFT) Polymerization

We presents an article about a micro review of reversible addition/fragmentation chain transfer (RAFT) polymerization. RAFT (Reversible Addition/Fragmentation Chain Transfer) polymerization is a reversible deactivation radical polymerization (RDRP) and one of the more versatile methods for providing living characteristics to radical polymerization.

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Protocols

Typical Procedures for Polymerizing via RAFT

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.

Concepts and Tools for RAFT Polymerization

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

Typical Procedures for Polymerizing via ATRP

An article about the typical procedures for polymerizing via ATRP, which demonstrates that in the following two procedures describe two ATRP polymerization reactions as performed by Prof. Dave Hadddleton′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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