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426369 Sigma-Aldrich

TEMPO

purified by sublimation, 99%

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

  • CAS Number 2564-83-2

  • Empirical Formula (Hill Notation) C9H18NO

  • Molecular Weight 156.25

  •  Beilstein/REAXYS Number 1422418

  •  EC Number 219-888-8

  •  MDL number MFCD00009599

  •  PubChem Substance ID 24866699

  •  NACRES NA.22

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Properties

Related Categories Chemical Synthesis, Materials Science, NMP Initiators, Other Oxidizing Agents, Oxidizing Agents,
assay   99%
purified by   sublimation
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

Description

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.

Packaging

1, 5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
GHS05  GHS05
Signal word 
Danger
Hazard statements 
RIDADR 
UN 3263 8 / PGII
WGK Germany 
WGK 3
RTECS 
TN8991900
Flash Point(F) 
152.6 °F
Flash Point(C) 
67 °C

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

A micro review of reversible addition/fragmentation chain transfer (RAFT) polymerization

Reversible addition/fragmentation chain transfer (RAFT) polymerization is a reversible deactivation radical polymerization (RDRP) and one of the more versatile methods for providing living characteri...
Keywords: Biomaterials, Living polymerization, Nanotechnology, Polymerization reactions, Radical polymerization, Reversible addition-fragmentation chain transfer polymerizations, transformation

Applying ARGET ATRP to the Growth of Polymer Brush Thin Films by Surface-initiated Polymerization

In 2006, Matyjaszewski and co-workers first described controlled radical polymerization by Activators ReGenerated by Electron Transfer Atom Transfer Radical Polymerization (ARGET ATRP),1-3 a developm...
Keywords: Antimicrobials, Ligands, Nanotubes, Oxidations, Polymerization reactions, Radical polymerization, Reductions, Reversible addition-fragmentation chain transfer polymerizations, Solution polymerization, Solvents

Block Copolymer Synthesis: NMP Approach

Nam S. Lee and Karen L. Wooley* Departments of Chemistry and Chemical Engineering Texas A&M University, P.O. Box 30012, 3255 TAMU, College Station, TX 77842-3012 *email: wooley@chem.tamu.edu
Keywords: Nanotechnology, Nuclear magnetic resonance spectroscopy, Polymerization reactions, Precipitation, Radical polymerization

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

Controlled radical polymerization, which provides exquisite tuning of macromolecular size, structure, composition and architecture, with experimental convenience, has become one of the most indispens...
Nam S. Lee and Karen L. Wooley*
Material Matters 2010, 5.1, 9.
Keywords: Building blocks, Nanotechnology, Nuclear magnetic resonance spectroscopy, Polymerization reactions, Precipitation, Radical polymerization, Reversible addition-fragmentation chain transfer polymerizations

Concepts and Tools for RAFT Polymerization

Reversible addition/fragmentation chain transfer (RAFT) is a form of living radical polymerization. RAFT polymerization was discovered at CSIRO in 1998.1 It soon became the focus of intensive researc...
Keywords: Polymerization reactions, Radical polymerization, Reversible addition-fragmentation chain transfer polymerizations

Copper(I)-mediated Living Radical Polymerization in the Presence of Pyridylmethanimine Ligands

Emergence of living radical polymerization mediated by transition metal catalysts in 1995 was a seminal piece of work in the field of synthetic polymer chemistry.1-3 Since this date, many transition ...
Keywords: Catalysis, Condensations, Evaporation, Filtration, Ligands, Oxidations, Polymer science, Polymerization reactions, Precipitation, Purification, Radical polymerization, Reductions, Solvents

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 discovere...
Keywords: Aerobic, Capillary electrophoresis, Catalysis, Chromatography, Coupling reactions, Oxidations, Polymerization reactions, Size-exclusion chromatography, Solvents

Tools for Performing ATRP (Atom Transfer Radical Polymerization)

Controlled radical polymerization (CRP) techniques have been reviewed in a number of articles1,2 and books,3 and include nitroxide-mediated polymerization (NMP),4-7 reversible addition fragmentation ...
Sebastian Grajales
Keywords: Ligands, Polymerization reactions, Purification, Radical polymerization, Reversible addition-fragmentation chain transfer polymerizations, Solution polymerization

Typical Procedures for Polymerizing via ATRP

The following two procedures describe two ATRP polymerization reactions as performed by Prof. Dave Hadddleton′s research group at the University of Warwick.
Keywords: Gas chromatography, Ligands, Nuclear magnetic resonance spectroscopy, Polymerization reactions, Size-exclusion chromatography, Solvents

Typical Procedures for Polymerizing via RAFT

RAFT (Reversible Addition/Fragmentation Chain Transfer) is a form of living radical polymerization involving conventional free radical polymerization of a substituted monomer in the presence of a sui...
Keywords: Nuclear magnetic resonance spectroscopy, Polymerization reactions, Radical polymerization, Reversible addition-fragmentation chain transfer polymerizations

Peer-Reviewed Papers
15

References

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