188526-94-5

Basic information

• Product Name: N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)aminoxyl
• Synonyms: N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)aminoxyl
• CAS NO: 188526-94-5
• Molecular Weight: 294.351
• Mol File: 188526-94-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)aminoxyl(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)aminoxyl(188526-94-5)
• EPA Substance Registry System: N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)aminoxyl(188526-94-5)

Safety Data

• Hazardous Substances Data: 188526-94-5(Hazardous Substances Data)

Upstream product

• 104-15-4 toluene-4-sulfonic acid 
• 2564-83-2 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical 

Downstream Products

• 224575-62-6 2,2,5,5-tetramethyl-3-(1-phenylethoxy)-4-diethylphosphono-3-azahexane 
• 654636-62-1 N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl)-O-(2-carboxyprop-2-yl)hydroxylamide 

Relevant articles and documents

Chemically triggered C-ON bond homolysis in alkoxyamines. 6. Effect of the counteranion

We showed (J. Org. Chem. 2012, 77) 9634) that the activation by methylation of pyridyl-based alkoxyamine 1 increased with the hydrogen bond donor properties of solvents. In this paper, activation of 1 by protonation with acids, CF3COOH and CSA, in tert-butylbenzene (t-BuPh) and in H 2O/MeOH afforded, with CF3COOH, kd 28-fold larger in H2O/MeOH than in t-BuPh, whereas it was only 4-fold larger when CSA was used. This puzzling observation was ascribed to the dissociation of the intimate ion pair.

Alkoxyamine C-ON bond homolysis: Stereoelectronic effects

Alkoxyamines and persistent nitroxides are important regulators of nitroxide-mediated radical polymerization (NMP) reactions. Because polymerization times decrease with an increase in the rate constant for the homolysis of the C-ON bond between the polyme

Factors influencing C-ON bond homolysis in alkoxyamines: Unexpected behavior of SG1 (N-(2-methyl-2-propyl)-N-(1-diethylphosphono-2,2-dimethylpropyl) -N-oxyl)-based alkoxyamines

Alkoxyamines and persistent nitroxides are important regulators of nitroxide-mediated radical polymerization (NMP). Since the polymerization time decreases with the increasing equilibrium constant K (kdk c), i.e., the increasing rate constant kd of the homolysis of the C-ON bond between the polymer chain and the nitroxide moiety, the factors influencing the cleavage rate constants are of considerable interest. SG1-based alkoxyamines have turned out to be the most potent alkoxyamine family to use for NMP of various monomers. Therefore, it is of high interest to determine the factors which make SG1 derivatives better regulators than TEMPO (2,2,6,6-tetramethylpiperidine-N-oxyl) derivatives. Contrary to what we had observed with TEMPO derivatives, we observed two relationships for the plot Ea vs BDE(C-H), one for the nonpolar released alkyl radicals (E a (kJ/mol) = -133.0 + 0.72BDE) and the other one for the polar released alkyl radicals (Ea (kJ/mol) = -137.0 + 0.69BDE). However, for both families (SG1 and TEMPO derivatives), the rate constants kd of the C-ON bond homolysis were correlated to the cleavage temperature T c (log(kd(s-1)) = 1.51 -0.058Tc). Such correlations should help to design new alkoxyamines to use as regulators and to improve the tuning of NMP experiments.