95407-69-5

Basic information

• Product Name: 4-METHOXY-2,2,6,6-TETRAMETHYLPIPERIDINE 1-OXYL
• Synonyms: Methoxytetramethylpiperidineoxyl;4-Methoxy-TEMPO 97%;4-Methoxy-2,2,6,6-tetramethylpiperidine 1-Oxyl 4-METHOXY-2,2,6,6-TETRAMETHYL-1-PIPERIDINYLOXY, FREE RADICAL;4-METHOXY-2,2,6,6-TETRAMETHYLPIPERIDINE 1-OXYL;4-METHOXY-TEMPO;4-METHOXY-TEMPO, FREE RADICAL;4-methoxy-2,2,6,6-tetramethylpiperidinyl-1-oxy
• CAS NO: 95407-69-5
• Molecular Formula: C₁₀H₂₀NO₂
• Molecular Weight: 186.27
• EINECS: -0
• Product Categories: Analytical Chemistry;ESR Spectrometry;Oxidation;Spin Labels;Synthetic Organic Chemistry
• Mol File: 95407-69-5.mol
• Article Data: 8

Chemical Properties

• Melting Point: 40.5-44 °C(lit.)
• Boiling Point: 242.1°Cat760mmHg
• Flash Point: 100.2°C
• Appearance: /
• Density: g/cm³
• Storage Temp.: 2-8°C
• BRN: 4740399
• CAS DataBase Reference: 4-METHOXY-2,2,6,6-TETRAMETHYLPIPERIDINE 1-OXYL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHOXY-2,2,6,6-TETRAMETHYLPIPERIDINE 1-OXYL(95407-69-5)
• EPA Substance Registry System: 4-METHOXY-2,2,6,6-TETRAMETHYLPIPERIDINE 1-OXYL(95407-69-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 95407-69-5(Hazardous Substances Data)

Usage

Description

4-Methoxy-TEMPO, also known as 4-Methoxy-2,2,6,6-tetramethyl-1-piperidinyloxy, is an aminoxyl free radical that is commonly used for the oxidation of alcohols, both primary and secondary. It has been proposed as a model compound for hindered amine light stabilizers (HALS). Its interaction with photocatalytic nanoparticulate titanium dioxide has been studied using electron spin resonance (ESR) and electrospray ionization mass spectrometry (ESI-MS) techniques.

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

• 90246-27-8 4-methoxy-1-oxo-2,2,6,6-tetramethylpiperidinium bromide 
• 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 
• 1048979-79-8 1-hydroxy-4-methoxy-2,2,6,6-tetramethylpiperidinium chloride 
• 131452-29-4 2,2,6,6-tetramethyl-N-hydroxy-4-methoxypiperidine 
• 45985-26-0 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl 
• 1174447-42-7 4-MeO-TEMPO-D 

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 
• 5042-53-5 1-(phenylsulfanyl)acetone 
• 5388-11-4 3-benzyl-3H-quinazolin-4-one 
• 1384194-58-4 N-tert-butoxy-4-methoxy-2,2,6,6-tetramethylpiperidine 

Relevant articles and documents

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.

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.