95407-69-5

Usage

Uses

Used in Chemical Synthesis:
4-Methoxy-TEMPO is used as a catalyst for the synthesis of 2-substituted benzoxazoles via aerobic oxidation reactions. This application takes advantage of its catalytic properties to facilitate the formation of desired chemical compounds.
Used in Oxidation Reactions:
In the field of organic chemistry, 4-Methoxy-TEMPO serves as a catalyst for the oxidation of alcohols. Its use as a catalyst allows for efficient and selective oxidation processes, which is crucial for the synthesis of various organic compounds.
Used in Stabilizer Research:
As a proposed hindered amine light stabilizer (HALS) model compound, 4-Methoxy-TEMPO is utilized in research to understand and develop new stabilizers for materials that are sensitive to light-induced degradation. This research is particularly relevant in the plastics and coatings industries.
Used in Photocatalysis Studies:
4-Methoxy-TEMPO's interaction with photocatalytic nanoparticulate titanium dioxide has been investigated for its potential applications in photocatalysis. This research could lead to advancements in environmental remediation and energy production.

InChI:InChI=1/C10H20NO2/c1-9(2)6-8(13-5)7-10(3,4)11(9)12/h8H,6-7H2,1-5H3

Upstream product

• 45985-24-8 TEMPOL 
• 74-88-4 methyl iodide 
• 31366-25-3 tetrathiafulvalene 
• 95407-70-8 1-oxo-4-methoxy-2,2,6,6-tetramethylpiperidinium chloride 
• 45985-26-0 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl 
• 1174447-42-7 4-MeO-TEMPO-D 
• 131452-29-4 2,2,6,6-tetramethyl-N-hydroxy-4-methoxypiperidine 
• 1048979-79-8 1-hydroxy-4-methoxy-2,2,6,6-tetramethylpiperidinium chloride 
• 90246-27-8 4-methoxy-1-oxo-2,2,6,6-tetramethylpiperidinium bromide 

Downstream Products

• 45985-26-0 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl 
• 1174447-42-7 4-MeO-TEMPO-D 
• 131452-29-4 2,2,6,6-tetramethyl-N-hydroxy-4-methoxypiperidine 
• 5388-11-4 3-benzyl-3H-quinazolin-4-one 
• 1384194-58-4 N-tert-butoxy-4-methoxy-2,2,6,6-tetramethylpiperidine 
• 5042-53-5 1-(phenylsulfanyl)acetone 

Relevant academic research and scientific papers

Convenient Synthesis of Bis-1,3-dithiolium Salts by One-electron Oxidation of Tetrathiafulvalene with Oxoaminium Salts

Several bis-1,3-dithiolium salts, radical cation salts of tetrathiafulvalene were synthesized in quantitative yields by oxidation of tetrathiafulvalene with oxoaminium salts for 1 min at room temperature.

Nickel-Catalyzed Aminoxylation of Inert Aliphatic C(sp3)-H Bonds with Stable Nitroxyl Radicals under Air: One-Pot Route to α-Formyl Acid Derivatives

Nickel-catalyzed aminoxylation of an unactivated C(sp3)-H bond with a stable nitroxyl radical has been accomplished for the first time to offer various N-alkoxyamine derivatives, which further enables a one-pot approach to α-formyl acid derivatives. The aminoxylation process reported also provides direct evidence for the oxidative addition of a cyclometallic intermediate with a free radical, which is helpful for the reaction-mechanism study in transition-metal-catalyzed functionalization of inert C(sp3)-H bonds.

Kinetics and thermodynamics of reversible disproportionation-comproportionation in redox triad oxoammonium cations - Nitroxyl radicals - Hydroxylamines

Kinetics and equilibrium of the acid-catalyzed disproportionation of cyclic nitroxyl radicals R2NO· to oxoammonium cations R2NO+ and hydroxylamines R2NOH is defined by redox and acid-base properties of these compounds. In a recent work (J. Phys. Org. Chem. 2014, 27, 114-120), we showed that the kinetic stability of R2NO· in acidic media depends on the basicity of the nitroxyl group. Here, we examined the kinetics of the reverse comproportionation reaction of R2NO+ and R2NOH to R2NO· and found that increasing in -I-effects of substituents greatly reduces the overall equilibrium constant of the reaction K4. This occurs because of both the increase of acidity constants of hydroxyammonium cations K3H+ and the difference between the reduction potentials of oxoammonium cations ER2NO+/R2NO· and nitroxyl radicals ER2NO·/R2NOH. pH dependences of reduction potentials of nitroxyl radicals to hydroxylamines E1/3σ and bond dissociation energies D(O-H) for hydroxylamines R2NOH inwater were determined. For a wide variety of piperidine- and pyrrolidine-1-oxyls values of pK3H+ and ER2NO+/R2NO· correlate with each other, as well aswith the equilibriumconstants K4 and the inductive substituent constants ωI. The correlations obtained allowprediction of the acid-base and redox characteristics of redox triads R2NO·-R2NO+-R2NOH.

Synthesis, crystal structure and fluorescence behavior of 2,6-Di(thiophen-2-yl)-benzo[1,2-d:4,5-d']bisoxazole

An effective and clean new aerobic approach for the synthesis of 2,6-disubstituted benzobisoxazole by using a one-pot reaction of an organic aminoxyl radical as the catalyst is reported. 2,6- Di(thiophen-2-yl)-benzo[1,2-d : 4,5-d]bisoxazole was synthesized with catalysis by the free radical 4-methoxy-TEMPO and characterized by 1H and 13C NMR spectroscopy, HRMS, as well as by elemental analysis, UV/Vis and emission spectroscopy. The crystal structure of the title compound has been determined by single-crystal X-ray diffraction. It crystallizes in the monoclinic space groupC2/c with a=12.531(1), b=3.8960(2), c = 28.733(2) A, β = 100:760(1), Z = 4. Through intermolecular weak C-H O hydrogen bonding and p-p stacking interactions, a supramolecular 3D structure is formed.

Nitroxyl radical plus hydroxylamine pseudo self-exchange reactions: Tunneling in hydrogen atom transfer

Bimolecular rate constants have been measured for reactions that involve hydrogen atom transfer (HAT) from hydroxylamines to nitroxyl radicals, using the stable radicals TEMPO· (2,2,6,6-tetramethylpiperidine-1-oxyl radical), 4-oxo-TEMPO·/