66893-81-0

Basic information

• Product Name: POBN
• Synonyms: α-(4-Pyridyl N-oxide)-N-tert-butylnitrone,N-(4-Pyridylmethylene)-tert-butylamine N,N′-dioxide, N-tert-Butyl-α-(4-pyridyl)nitrone N′-oxide, POBN;alpha-(4-Pyridyl 1-oxide)-N-tert-butyl-nitrone, 99% 100MG;N-tert-Butyl-α-(4-pyridyl)nitrone Nμ-oxide;N-tert-Butyl-alpha-(4-pyridyl)nitrone N'-Oxide POBN N-(4-Pyridylmethylene)-tert-butylamine N,N'-Dioxide alpha-(4-Pyridyl N-Oxide)-N-tert-butylnitrone;alpha-(4-Pyridyl N-oxide)-N-tert-butylnitrone ~95%;Dimethylaminoparthenolide/ Tert-Butyl-[(1-Oxido-4-Pyridylidene)Methyl]-Oxo-Ammonium;alpha-(4-Pyridyl N-oxide)-N-tert-butylnitrone 99%;-(4-pyridyl-1-oxide)nitrone
• CAS NO: 66893-81-0
• Molecular Formula: C₁₀H₁₄N₂O₂
• Molecular Weight: 194.23
• EINECS: 266-512-3
• Product Categories: Analytical Reagents;Analytical/Chromatography;Building Blocks;C10;Chemical Synthesis;Electron Spin Resonance (ESR/EPR) Spectroscopy;Heterocyclic Building Blocks;Pyridines;Spectroscopy;Analytical Chemistry;ESR Spectrometry;Spin Trapping Reagents
• Mol File: 66893-81-0.mol

Chemical Properties

• Melting Point: 183-185 °C(lit.)
• Boiling Point: 330.68°C (rough estimate)
• Flash Point: 201.219ºC
• Appearance: White to off-white crystalline solid.
• Density: 1.1444 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.5000 (estimate)
• Storage Temp.: 2-8°C
• Solubility: water: soluble10mg/mL, clear, colorless to faintly yellow
• PKA: 0.76±0.53(Predicted)
• BRN: 1453764
• CAS DataBase Reference: POBN(CAS DataBase Reference)
• NIST Chemistry Reference: POBN(66893-81-0)
• EPA Substance Registry System: POBN(66893-81-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 66893-81-0(Hazardous Substances Data)

Usage

Uses

Used in Antioxidant Research:
POBN is used as a spin trap reagent for detecting and measuring the formation of free radicals, such as the 1-hydroxyethyl radical (HER), which can bind to proteins. This application is particularly relevant in studying the oxidation of ethanol and the formation of hydroxyl radicals in chondrocytes and cartilage.
Used in DNA Methylation Studies:
POBN is employed as a research tool in the investigation of DNA methylation, a crucial epigenetic modification that plays a significant role in gene regulation and various biological processes.
Used in Iron-Mediated Polyunsaturated Fatty Acid Peroxidation Studies:
POBN is used as a spin trap in the study of iron-mediated polyunsaturated fatty acid peroxidation, a process that can lead to cellular damage and has been implicated in various diseases.
Used in Alzheimer's Disease Research:
POBN is utilized in research on Alzheimer's disease, specifically in studying the free-radical formation by Alzheimer β-amyloid peptide, which is associated with the pathogenesis of the disease.
Used in Pharmaceutical and Chemical Industries:
POBN is used as a research compound in the pharmaceutical and chemical industries for the development of new drugs and the study of various chemical reactions involving free radicals.

InChI:InChI=1/C10H14N2O2/c1-10(2,3)12(14)8-9-4-6-11(13)7-5-9/h4-8H,1-3H3/b12-8-

Upstream product

• 7216-42-4 isonicotinaldehyde 1-oxide 
• 57497-39-9 N-tertbutylhydroxylamine hydrochloride 
• 16649-50-6 N-tert-Butylhydroxylamine 

Downstream Products

• 1224720-35-7 C₂₄H₃₃N₂O₅ 
• 7216-42-4 isonicotinaldehyde 1-oxide 
• 16649-50-6 N-tert-Butylhydroxylamine 

Relevant articles and documents

Spin Trapping of Hydroxyl Radical in the Troposphere for Determination by Electron Spin Resonance and Gas Chromatography/Mass Spectrometry

An airborne sampling system using a spin trapping method has been developed to determine the concentration of hydroxyl radical in the troposphere.Hydroxyl radical was trapped in a α-4-pyridyl-N-tert-butylnitrone α-1-oxide (4-POBN) in situ to form a stable hydroxy adduct of 4-POBN and determined by electron spin resonance (ESR) later in the laboratory.The concentration of hydroxyl radical ranged from less than 5E5 molecules/cm3 at an altitude of 10 km to a maximum of 5E6 molecules/cm3 at an altitude of 6 km at 37N 140E during the period of May 1980 to Feb 1981.The limit of detection of the present system was about 5E5 molecules/cm3 if 200 m3 of air was sampled.The uncertainty of the concentration was estimated to be less than 30percent.

Dipole-stabilized carbanions in the series of cyclic aldonitrones 3. The influence of the configuration of the nitrone group on H-D exchange of the methine hydrogen atom and metallation of aldonitrones

The spin-spin coupling constants 3JC,H between the hydrogen atom of the aldonitrone group and the carbon atom bound to the nitrogen atom of the N-oxide fragment were determined for a wide range of cyclic and acyclic aldonitrones. Based on comparison of these constants (trans-3JC,H (E isomer) > cis-3JC,H (Z isomer)), the Z configuration was assigned to acyclic nitrones. Coordination of organolithium compounds to the oxygen atom of the N->O group was revealed by 13C NMR spectroscopy. This coordination is the necessary condition for the metallation of aldonitrones. The configuration of the nitrone group is responsible for the ability of the F form of acyclic aldonitrones to undergo CD3ONa-catalyzed isotope exchange of the methine proton in CD3OD and metallation with BusLi.