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
• Article Data: 5

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

Different sources of media describe the Uses of 37149-18-1 differently. You can refer to the following data:
1. 4-Carboxy-TEMPO may be employed as catalyst for the oxidation of regenerated cellulose (viscose rayon) to cellouronic acid. 4-Carboxy-TEMPO is a 4-substituted 2,2,6,6-tetramethylpiperidyl-1-oxy (TEMPO) derivative. 4-carboxy-TEMPO immobilized with 3-aminopropylsilane on the mesoporous silica surface comprises heterogeneous catalytic system employed for various oxidation reactions.
2. 4-Carboxy-TEMPO may be employed as catalyst for the oxidation of regenerated cellulose (viscose rayon) to cellouronic acid.

General Description

4-Carboxy-TEMPO is a 4-substituted 2,2,6,6-tetramethylpiperidyl-1-oxy (TEMPO) derivative. 4-carboxy-TEMPO immobilized with 3-aminopropylsilane on the mesoporous silica surface comprises heterogeneous catalytic system employed for various oxidation reactions.

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

• 106946-95-6 iron(III) 5,10,15,20-tetra-p-tolylporphyrin 2,2,6,6-tetramethyl-1-oxypiperidine-4-carboxylate 
• 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.

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.

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).