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Merck
CN

730297

TEMPO methacrylate

97%

Synonym(s):

4-Methacryloyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl, PTMA monomer

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About This Item

Empirical Formula (Hill Notation):
C13H22NO3
CAS Number:
15051-46-4
Molecular Weight:
240.32
NACRES:
NA.23
PubChem Substance ID:
329764552
UNSPSC Code:
12162002
MDL number:
MFCD17677357

Key Documents

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InChI

1S/C13H22NO3/c1-9(2)11(15)17-10-7-12(3,4)14(16)13(5,6)8-10/h10H,1,7-8H2,2-6H3

SMILES string

CC(=C)C(=O)OC1CC(C)(C)N([O])C(C)(C)C1

InChI key

BTWSPOZXDCFMLX-UHFFFAOYSA-N

assay

97%

form

powder

mp

86-90 °C

storage temp.

2-8°C

General description

TEMPO methacrylate (4-Methacryloyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl) undergoes anionic dispersion polymerization to afford nanometer-sized polymer particles bearing 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) radicals.

Application

Stable nitroxide radical useful in controlling living radical polymerizations, with a methacrylate functionality for cross-linking or orthogonal polymerization.
TEMPO methacrylate (4-Methacryloyloxy-2,2,6,6-tetramethylpiperidine-1-oxyl) may be employed as counter radical for polymerization of styrene.

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

hcodes

H317,H411

Hazard Classifications

Aquatic Chronic 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP9189
MKCP8329
MKCN3298
MKCN0233
MKCC6925

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Magnetic force microscopic images of nanometer-sized polyradical particles.
Michinobu T, et al.
Polymer Journal, 35(1), 71-75 (2003)
Nakahara, K.; Iwasa, S.; Satoh, M.; Morioka, Y.; Iriyama, J.; Suguro, M.; Hasegawa, E.
Chemical Physics Letters, 359, 351-351 (2002)
Controlled radical polymerization of styrene in the presence of a polymerizable nitroxide compound.
Li C, et al.
Macromolecules, 32(21), 7012-7014 (1999)
Battery-inspired, nonvolatile, and rewritable memory architecture: a radical polymer-based organic device.
Yasunori Yonekuta et al.
Journal of the American Chemical Society, 129(46), 14128-14129 (2007-10-30)

Articles

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

Micro Review of RAFT Polymerization

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

TEMPO催化氧化

TEMPO（2,2,6,6-四甲基哌啶氧基或2,2,6,6-四甲基哌啶1-氧基）及其衍生物在有机氧化反应催化剂中可以作为稳定的硝酰基使用。TEMPO由Lebedev和Kazarnovskii于1960年发现，其具有的稳定自由基性质得益于其庞大的取代基团阻碍了自由基与其他分子之间发生反应。

Protocols

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.

Polymerizing via ATRP

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

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.

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