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.

2′-Alkynylnucleotides: A Sequence- and Spin Label-Flexible Strategy for EPR Spectroscopy in DNA

Electron paramagnetic resonance (EPR) spectroscopy is a powerful method to elucidate molecular structure through the measurement of distances between conformationally well-defined spin labels. Here we report a sequence-flexible approach to the synthesis of double spin-labeled DNA duplexes, where 2′-alkynylnucleosides are incorporated at terminal and internal positions on complementary strands. Post-DNA synthesis copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions with a variety of spin labels enable the use of double electron-electron resonance experiments to measure a number of distances on the duplex, affording a high level of detailed structural information.

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.