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730297

Sigma-Aldrich

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
MDL number:
MFCD17677357
UNSPSC Code:
12162002
PubChem Substance ID:
329764552
NACRES:
NA.23

assay

97%

form

powder

mp

86-90 °C

storage temp.

2-8°C

SMILES string

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

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

InChI key

BTWSPOZXDCFMLX-UHFFFAOYSA-N

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.[1]

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.[2]

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

hcodes

H317,H411

Hazard Classifications

Aquatic Chronic 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

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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4-Hydroxy-TEMPO benzoate, free radical 97%

Sigma-Aldrich

371343

4-Hydroxy-TEMPO benzoate, free radical

Controlled radical polymerization of styrene in the presence of a polymerizable nitroxide compound.
Li C, et al.
Macromolecules, 32(21), 7012-7014 (1999)
Nakahara, K.; Iwasa, S.; Satoh, M.; Morioka, Y.; Iriyama, J.; Suguro, M.; Hasegawa, E.
Chemical Physics Letters, 359, 351-351 (2002)
Magnetic force microscopic images of nanometer-sized polyradical particles.
Michinobu T, et al.
Polymer Journal, 35(1), 71-75 (2003)
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.

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.

Polymerizing via ATRP

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

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