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426369

Sigma-Aldrich

TEMPO

purified by sublimation, 99%

Sinonimo/i:

2,2,6,6-Tetramethylpiperidine 1-oxyl, 2,2,6,6-Tetramethyl-1-piperidinyloxy, free radical, TEMPO

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About This Item

Formula empirica (notazione di Hill):
C9H18NO
Numero CAS:
2564-83-2
Peso molecolare:
156.25
Beilstein:
1422418
Numero CE:
219-888-8
Numero MDL:
MFCD00009599
Codice UNSPSC:
12352119
ID PubChem:
24866699
NACRES:
NA.22

Livello qualitativo

200

Saggio

99%

Stato

solid

Purificato mediante

sublimation

Impiego in reazioni chimiche

reagent type: oxidant

Punto di fusione

36-38 °C (lit.)

Temperatura di conservazione

2-8°C

Stringa SMILE

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
QYTDEUPAUMOIOP-UHFFFAOYSA-N

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Descrizione generale

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

Applicazioni

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.

Pittogrammi

Corrosion
GHS05

Avvertenze

Danger

Indicazioni di pericolo

H314,H412

Classi di pericolo

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

Codice della classe di stoccaggio

8A - Combustible corrosive hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 2

Punto d’infiammabilità (°F)

152.6 °F - closed cup

Punto d’infiammabilità (°C)

67 °C - closed cup

Dispositivi di protezione individuale

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificati d'analisi (COA)

Lot/Batch Number
MKCB0475V
MKBJ7394V
MKBW0278V
MKBR7572V
MKBW6930V

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MitoTEMPO ≥98% (HPLC)

Sigma-Aldrich

SML0737

MitoTEMPO

4-Acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl purum, ≥98.0% (HPLC)

Sigma-Aldrich

00375

4-Acetamido-2,2,6,6-tetramethylpiperidine 1-oxyl

4-Oxo-TEMPO-d16, free radical for ESR-spectroscopy, 97 atom % D

Sigma-Aldrich

485268

4-Oxo-TEMPO-d16, free radical

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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Articoli

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

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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Protocolli

Concepts and Tools for RAFT Polymerization

Sigma-Aldrich presents an article about RAFT, or Reversible Addition/Fragmentation Chain Transfer, which is a form of living radical polymerization.

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.

Typical Procedures for Polymerizing via ATRP

Sigma-Aldrich presents 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.

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