37149-18-1

Basic information

• Product Name: 4-CARBOXY-2,2,6,6-TETRAMETHYLPIPERIDINE 1-OXYL
• Synonyms: 4-CARBOXY-TEMPO;4-CARBOXY-2,2,6,6-TETRAMETHYLPIPERIDINE 1-OXYL;4-CARBOXY-2,2,6,6-TETRAMETHYLPIPERIDINYLOXY;RARECHEM AL BO 1387;4-CARBOXY-TEMPO, FREE RADICAL, 97%;4-Carboxy-2,2,6,6-tetramethylpiperidine1-oxylfreeradical[spinlabel];4-CARBOXY-2,2,6,6-TETRAMETHYLPIPERIDINE 1-OXYL, FREE RADICAL;4-carboxy-2,2,6,6-tetramethylpiperidinyloxy, free radical
• CAS NO: 37149-18-1
• Molecular Formula: C₁₀H₁₈NO₃
• Molecular Weight: 200.25
• Product Categories: Analytical Chemistry;ESR Spectrometry;Spin Labels
• Mol File: 37149-18-1.mol

Chemical Properties

• Melting Point: 185-189 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Storage Temp.: 2-8°C
• BRN: 3949026
• CAS DataBase Reference: 4-CARBOXY-2,2,6,6-TETRAMETHYLPIPERIDINE 1-OXYL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CARBOXY-2,2,6,6-TETRAMETHYLPIPERIDINE 1-OXYL(37149-18-1)
• EPA Substance Registry System: 4-CARBOXY-2,2,6,6-TETRAMETHYLPIPERIDINE 1-OXYL(37149-18-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 37149-18-1(Hazardous Substances Data)

Usage

Uses

Used in Textile Industry:
4-Carboxy-TEMPO is used as a catalyst for the oxidation of regenerated cellulose (viscose rayon) to cellouronic acid. This process is essential for the production of high-quality textiles with enhanced properties, such as improved strength and durability.
Used in Heterogeneous Catalysis:
4-Carboxy-TEMPO immobilized with 3-aminopropylsilane on the mesoporous silica surface forms a heterogeneous catalytic system employed for various oxidation reactions. This system is particularly useful in the chemical industry for its ability to catalyze a wide range of oxidation processes, leading to more efficient and environmentally friendly production methods.

InChI:InChI=1/C10H18NO3/c1-9(2)5-7(8(12)13)6-10(3,4)11(9)14/h7H,5-6H2,1-4H3,(H,12,13)

Upstream product

• 37654-42-5 4-isocyano-2,2,6,6-tetramethylpiperidine-1-oxyl 
• 826-36-8 2,2,6,6-Tetramethyl-4-piperidone 
• 45985-26-0 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl 
• 38078-71-6 4-cyano-2,2,6,6-tetramethyl-piperidinyloxy 

Downstream Products

• 439858-36-3 1-hydroxy-4-carbamoyl-2,2,6,6,-tetramethylpiperidine methyl ester 
• 552321-58-1 C₃₉H₄₄N₃O₄ 
• 924653-87-2 4-[[[[4'-[(2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl][1,1'-biphenyl]-2-yl]sulfonyl]amino]carbonyl]-2,2,6,6-tetramethyl-1-piperidinyloxy 
• 106946-95-6 iron(III) 5,10,15,20-tetra-p-tolylporphyrin 2,2,6,6-tetramethyl-1-oxypiperidine-4-carboxylate 
• 1228254-15-6 1-oxyl-2,2,6,6-tetramethyl-piperidine-4-carboxylic acid[(2-(3,4-dimethoxyphenyl))-5-[[2-(3,4-dimethoxyphenyl)-ethyl]methylamino]-2-isopropyl]-pentylamide radical 
• 1246776-27-1 [3-(2,2,6,6-tetramethylpiperidine-1-oxyl-4-carboxamido)propyl] 5-acetamido-4,7,8-tri-O-acetyl-9-benzamido-3,5,9-trideoxy-D-glycero-α-D-galacto-2-nonulopyranosidic acid 
• 45985-26-0 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl 
• 1582289-15-3 p-methoxyphenyl O-{6-O-(TEMPO-4-carbonyl)}-β-D-glucoside 

Relevant articles and documents

Suspending Ion Electrocatalysts in Charged Metal–Organic Frameworks to Improve the Conductivity and Selectivity in Electroorganic Synthesis

Electroorganic synthesis is an environmentally friendly alternative to traditional synthetic methods; however, the application of this strategy is heavily hindered by low product selectivity. Metal–organic frameworks (MOFs) exhibit high selectivity in numerous catalytic reactions; however, poor conductivity heavily limits the application of MOFs in electroorganic synthesis. To realize the electrocatalytic application of MOFs in selective electroorganic synthesis, a practically applicable strategy by suspending ion electrocatalysts in charged MOFs is herein reported. This approach could markedly improve the product selectivity in electroorganic synthesis. In the electrocatalytic oxidative self-coupling of benzylamine experiments, the imine product selectivity is markedly improved from 61.3 to 94.9 %, when the MOF-based electrocatalyst is used instead of the corresponding homogeneous electrocatalyst under the identical conditions. Therefore, this work opens a new route to improve the product selectivity in electroorganic synthesis.

Synthesis and fluorescence properties of six fluorescein-nitroxide radical hybrid-compounds

Six fluorescein-nitroxide radical hybrid-compounds (2ab, 3ab, 4, and 5) were synthesized by the condensation of 5- or 6-carboxy-fluorescein and 4-amino-TEMPO (2ab), 5- or 6-aminofluorescein and 4-carboxy-TEMPO (3ab), and fluorescein and 4-carboxy-TEMPO (4), or by reaction of the 3-hydroxyl group of fluorescein with DPROXYL-3-ylmethyl methanesulfonate (5). Fluorescence intensities (around 520 nm) after reduction of the radical increased to 1.43-, 1.38-, and 1.61-folds for 2a, 2b and 3b respectively; 3a alone exhibited a decrease in intensity on reduction. Since 4 was readily solvolyzed in PBS or even methanol to afford fluorescein and 4-carboxy-TEMPO, its fluorescence change could not be measured. Hybrid compound 5 containing an ether-linkage between the fluorescein phenol and 3-hydroxymethyl-DPROXYL hydroxyl centers, was stable and on reduction, showed a maximum increase (3.21-fold) in relative fluorescence intensity in PBS (pH 5.0), despite its remarkably low absolute fluorescence intensity.

Spin-labelled diketopiperazines and peptide-peptoid chimera by Ugi-multi-component-reactions

For the first time, spin-labelled coumpounds have been obtained by isonitrile-based multi component reactions (IMCRs). The typical IMCR Ugi-protocols offer a simple experimental setup allowing structural variety by which labelled diketopiperazines (DKPs) and peptide-peptoid chimera have been synthesized. The reaction keeps the paramagnetic spin label intact and offers a simple and versatile route to a large variety of new and chemically diverse spin labels.

Highly efficient polarizing agents for dynamic nuclear polarization

The invention relates to compounds of general formula (I) wherein X is C=O or SO2, M is NR2 or O, and Q1 and Q2 are nitroxide-containing radicals, and their use as a Dynamic Nuclear Polarization (DNP) agent for polarizing an NMR-active spin of a nucleus of an analyte in Nuclear Magnetic Resonance (NMR) spectroscopy.

INFLUENCE OF CHEMICAL STRUCTURE OF NITROXYL SPIN LABELS ON THEIR REDUCTION BY ASCORBIC ACID

The influence of structure on the reduction of nitroxyl spin labels by ascorbic acid was examined using both piperidine and pyrrolidine nitroxyls.A five-fold molar excess of ascorbic acid and pH of 7.4 were used.The nitroxyl concentration was measured by electron spin resonance spectrometry.The five-membered (pyrrolidine) nitroxyls were more stable than the six-membered derivatives.Ring substituents also influenced the reaction.The anionic derivatives were more stable than the unionized compounds which, in turn, were more stable than the amines (cations at pH 7.4).