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426369

Sigma-Aldrich

TEMPO

purified by sublimation, 99%

Synonym(e):

2,2,6,6-Tetramethyl-piperidin-1-oxyl, 2,2,6,6-Tetramethyl-1-piperidinyloxy, freies Radikal, TEMPO

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About This Item

Empirische Formel (Hill-System):
C9H18NO
CAS-Nummer:
2564-83-2
Molekulargewicht:
156.25
Beilstein:
1422418
EG-Nummer:
219-888-8
MDL-Nummer:
MFCD00009599
UNSPSC-Code:
12352119
PubChem Substanz-ID:
24866699
NACRES:
NA.22

Assay

99%

Form

solid

Aufgereinigt durch

sublimation

Eignung der Reaktion

reagent type: oxidant

mp (Schmelzpunkt)

36-38 °C (lit.)

Lagertemp.

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

InChIKey

QYTDEUPAUMOIOP-UHFFFAOYSA-N

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Allgemeine Beschreibung

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

Anwendung

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.

Piktogramme

Corrosion
GHS05

Signalwort

Danger

H-Sätze

H314,H412

Gefahreneinstufungen

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

Lagerklassenschlüssel

8A - Combustible corrosive hazardous materials

WGK

WGK 2

Flammpunkt (°F)

152.6 °F - closed cup

Flammpunkt (°C)

67 °C - closed cup

Persönliche Schutzausrüstung

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

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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MitoTEMPO ≥98% (HPLC)

Sigma-Aldrich

SML0737

MitoTEMPO

4-Acetamino-TEMPO purum, ≥98.0% (HPLC)

Sigma-Aldrich

00375

4-Acetamino-TEMPO

4-Oxo-TEMPO-d16, freies Radikal for ESR-spectroscopy, 97 atom % D

Sigma-Aldrich

485268

4-Oxo-TEMPO-d16, freies Radikal

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
Alle zugehörigen Dokumente anzeigen

Artikel

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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Protokolle

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 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

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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