55738-75-5

Basic information

• Product Name: 3-hydroxymethyl-2,2,5,5-tetramethylpyrroline-N-oxyl
• Synonyms: 3-hydroxymethyl-2,2,5,5-tetramethylpyrroline-N-oxyl;2,5-dihydro-3-(hydroxyMethyl)-2,2,5,5-tetraMethyl-1H-Pyrrol-1-yloxy;3-HydroxyMethyl-2,2,5,5-tetraMethyl-3-pyrrolin-1-yloxy;3-HydroxyMethyl-2,2,5,5-tetraMethylpyrrolin-1-oxyl;2,5-dihydro-3-(hydroxyMethyl)-2,2,5,5-tetraMethyl-1H-Pyrrol-1-yloxy-15N, d15;3-HydroxyMethyl-(1-oxy-2,2,5,5-tetraMethylpyrroline)-15N, d15;3-HydroxyMethyl-2,2,5,5-tetraMethyl-3-pyrrolin-1-yloxy-15N, d15;3-HydroxyMethyl-2,2,5,5-tetraMethylpyrrolin-1-oxyl-15N, d15
• CAS NO: 55738-75-5
• Molecular Formula: C₉H₁₆NO₂
• Molecular Weight: 0
• Product Categories: Spin Labeling Compounds
• Mol File: 55738-75-5.mol
• Article Data: 13

Chemical Properties

• Melting Point: 63-65°C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• CAS DataBase Reference: 3-hydroxymethyl-2,2,5,5-tetramethylpyrroline-N-oxyl(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxymethyl-2,2,5,5-tetramethylpyrroline-N-oxyl(55738-75-5)
• EPA Substance Registry System: 3-hydroxymethyl-2,2,5,5-tetramethylpyrroline-N-oxyl(55738-75-5)

Safety Data

• Hazardous Substances Data: 55738-75-5(Hazardous Substances Data)

Usage

Description

3-Hydroxymethyl-2,2,5,5-tetramethylpyrroline-N-oxyl, also known as 3-Hydroxymethyl-(1-oxy-2,2,5,5-tetramethylpyrroline), is an organic compound with the chemical formula C9H17NO2. It is characterized by its unique structure, which includes a pyrroline ring with four methyl groups and a hydroxymethyl group attached to the nitrogen atom. 3-hydroxymethyl-2,2,5,5-tetramethylpyrroline-N-oxyl is known for its potential applications in various fields, particularly in organic synthesis.

Uses

Used in Organic Synthesis:
3-Hydroxymethyl-2,2,5,5-tetramethylpyrroline-N-oxyl is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure allows it to be a versatile building block in the synthesis of complex molecules, which can be further modified or functionalized to create a wide range of products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Hydroxymethyl-2,2,5,5-tetramethylpyrroline-N-oxyl can be used as a key component in the development of new drugs. Its ability to form stable radicals and its reactivity make it a promising candidate for the synthesis of novel therapeutic agents with potential applications in various medical conditions.
Used in Chemical Research:
3-Hydroxymethyl-2,2,5,5-tetramethylpyrroline-N-oxyl is also utilized in chemical research as a model compound to study the properties and reactivity of nitroxyl radicals. This knowledge can contribute to the development of new synthetic methods, catalysts, and materials with improved performance and applications in various industries.

InChI:InChI=1/C9H16NO2/c1-8(2)5-7(6-11)9(3,4)10(8)12/h5,11H,6H2,1-4H3

Upstream product

• 2154-32-7 methyl 1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-carboxylate radical 
• 19187-50-9 3-{[(ethoxycarbonyl)oxy]carbonyl}-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxy 
• 2154-67-8 3-carboxy-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxy 
• 76893-15-7 C₁₅H₁₃F₅NO₃ 
• 83078-59-5 C₁₇H₂₆NO₆ 
• 83078-58-4 diethyl (1-oxyl-2,2,5,5-tetramethyl-3-pyrroline-3-carbonyl)-malonate 
• 123665-64-5 (2,2,5,5-Tetramethyl-2,5-dihydro-1H-pyrrol-3-yl)-methanol 
• 826-36-8 2,2,6,6-Tetramethyl-4-piperidone 
• 57167-75-6 3,5-dibromo-2,2,6,6-tetramethylpiperidin-4-one 
• 70473-81-3 2,2,5,5-tetramethyl-2,5-dihydropyrrole-3-carboxylic acid methyl ester 
• 19971-12-1 3,5-Dibromo-4-oxo-2,2,6,6-tetramethylpiperidine Hydrobromide 

Downstream Products

• 133595-26-3 3-Acetoacetyloxymethyl-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrol-1-yloxy radical 
• 71051-83-7 3-formyl-2,2,5,5-tetramethyl-pyrroline-1-oxyl 
• 105843-22-9 (2,5-dihydro-2,2,5,5-tetramethyl-1-hydroxyl-1H-pyrrol-3-yl)methanol hydrogen chloride 
• 76893-31-7 1-Oxyl-2,2,5,5-tetramethyl-2,5-dihydropyrrole-3-ylmethyl benzoate 
• 149473-06-3 3-ethoxycarbonylmethyl-2,2,5,5-tetramethyl-4-methylenepyrrolidin-1-yloxy radical 
• 76893-27-1 (1-oxyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-3-yl)methyl methanesulfonate 
• 76893-28-2 C₁₅H₂₀NO₄S 
• 76893-29-3 2,5-dihydro-2,2,5,5-tetramethyl-3-({[(4-methylphenyl)sulfonyl]oxy}methyl)-1H-pyrrol-1-yloxy 
• 76893-30-6 C₁₅H₁₉BrNO₄S 
• 136573-75-6 4-methylene-3-<(methylthio)carbonylthio>-2,2,5,5-tetramethylpyrrolidin-1-yloxy radical 
• 160252-72-2 3-vinyloxymethyl-2,2,5,5-tetramethyl-2,5-dihydro-1H-pyrrol-1-yloxy radical 
• 173201-49-5 2,5-dihydro-2,2,5,5-tetramethyl-3-pivaloyloxymethyl-1H-pyrrol-1-yloxyl radical 
• 123665-64-5 (2,2,5,5-Tetramethyl-2,5-dihydro-1H-pyrrol-3-yl)-methanol 
• 170810-86-3 3-formyl-2,5-dihydro-2,2,5,5-tetramethyl-1H-pyrrole 

Relevant articles and documents

An efficient synthesis of 3-(N-piperidinemethyl)-2,2,5,5-tetramethyl-1-oxy-3-pyrroline, a promising radioprotector for cancer radiotherapy

Nitroxides can ameliorate the toxic effects of radiation during cancer therapy. Nitroxides are paramagnetic and can be used in magnetic resonance imaging (MRI) and electron paramagnetic resonance imaging (EPRI) to monitor in vivo oxidative stress status. Compound 5 (3-(N-piperidinemethyl)-2,2,5,5-tetramethyl-1-oxy-3-pyrroline) was found to be the most effective nitroxide radioprotector. An efficient synthesis for this promising radioprotector was developed.

Synthesis of Chiral Spin-Labeled Amino Acids

Spin-labeled amino acids (SLAAs) are often used to determine intermolecular distances and conformations in proteins via double electron-electron resonance. Currently available SLAAs can be difficult to incorporate selectively and have little resemblance to natural side chains in proteins. Enantioselective synthesis of three spin-labeled l-amino acids is described, starting from readily available 2,2,6,6-tetramethyl-4-piperidinone. These SLAAs better replicate canonical residues in proteins and aim for biological incorporation via genetic incorporation or solid-phase peptide 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.

Genetically Encoded Spin Label

The invention relates to a non-canonical amino acid of the formula I, namely A - L - X, A is a lysine or a tyrosine, L is a linker or absent, and X is an aminoxyl radical, and if A is lysine, L is bound to the N-epsilon atom of the lysine or, if L is absent, X is bound to the N-epsilon atom of the lysine; and if A is tyrosine, L is bound to the phenolic hydroxyl of the tyrosine or, if L is absent, X is bound to the phenolic hydroxyl of the tyrosine. Moreover, the invention also relates to a method for introducing a spin label into a protein and to a modified pyrrolysyl-tRNA-synthetase.