3376-24-7

Basic information

• Product Name: N-TERT-BUTYL-ALPHA-PHENYLNITRONE
• Synonyms: 2-methyl-n-(phenylmethylene)-2-propanaminn-oxide;2-methyl-n-(phenylmethylene)-s-propanaminen-oxide;2-methyl-n-(phenylmethylene)-s-propanaminn-oxide;2-phenyl-n-tert-butylnitrone;alpha-phenyl-n-tert-butylnitrone;Benzylidene(tert-butyl)azane oxide;benzylidene-tert-butylaminen-oxide;c-phenyl-n-tert-butylnitrone
• CAS NO: 3376-24-7
• Molecular Formula: C₁₁H₁₅NO
• Molecular Weight: 177.24
• EINECS: 222-168-6
• Product Categories: Spin Trapping Reagents;Analytical Chemistry;ESR Spectrometry
• Mol File: 3376-24-7.mol
• Article Data: 72

Chemical Properties

• Melting Point: 73-74 °C(lit.)
• Boiling Point: 283℃
• Flash Point: 119℃
• Appearance: white/powder
• Density: 0.990
• Vapor Pressure: 0.00547mmHg at 25°C
• Refractive Index: 1.5480 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO: soluble
• PKA: 1.50±0.53(Predicted)
• Water Solubility: Soluble in DMSO (10 mg/ml), chloroform (50 mg/ml), and water (20 mg/ml).
• Merck: 14,7056
• BRN: 2044028
• CAS DataBase Reference: N-TERT-BUTYL-ALPHA-PHENYLNITRONE(CAS DataBase Reference)
• NIST Chemistry Reference: N-TERT-BUTYL-ALPHA-PHENYLNITRONE(3376-24-7)
• EPA Substance Registry System: N-TERT-BUTYL-ALPHA-PHENYLNITRONE(3376-24-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: TX1760000
• F: 10
• TSCA: Yes
• Hazardous Substances Data: 3376-24-7(Hazardous Substances Data)

Usage

Description

N-TERT-BUTYL-ALPHA-PHENYLNITRONE, also known as PBN, is a widely recognized free radical trap and a potent antioxidant. It is a white to light beige fine crystalline powder that has been demonstrated to act as a protective agent in various experimental models of neurodegenerative disorders. PBN is effective in inhibiting lipid peroxidation in rat liver microsomes and preventing the induction of inducible nitric oxide synthase (iNOS) by reactive oxygen species.

Uses

Used in Antioxidant Applications:
N-TERT-BUTYL-ALPHA-PHENYLNITRONE is used as an antioxidant for its ability to scavenge free radicals and protect cells from oxidative damage, which is particularly important in the context of neurodegenerative disorders.
Used in Chemical Preservation:
In the field of molecular biology, N-TERT-BUTYL-ALPHA-PHENYLNITRONE is used as a component of Dneasy Blood&Tissue buffer to preserve the oxidized state of DNA extracted from human non-tumorigenic epithelial breast (MCF10A) cells.
Used in Cellular Research:
N-TERT-BUTYL-ALPHA-PHENYLNITRONE is used as a free radical scavenger of reactive oxygen species (ROS) in microglial (MG) cell lines, which helps in studying the role of oxidative stress in cellular processes.
Used in Cancer Research:
In the field of cancer research, N-TERT-BUTYL-ALPHA-PHENYLNITRONE is used to attenuate fibroblast senescence in unstable oral squamous cell carcinomas (GU-OSCC), providing insights into the role of oxidative stress in cancer progression.
Used in Pharmaceutical Industry:
N-TERT-BUTYL-ALPHA-PHENYLNITRONE is used as a spin trap reagent for carbon-, oxygen-, or nitrogen-centered free radicals in the development of pharmaceuticals targeting various diseases and conditions related to oxidative stress.
Used in Neurodegenerative Research:
In the field of neurodegenerative research, N-TERT-BUTYL-ALPHA-PHENYLNITRONE is used as a protective agent in experimental models to study its potential in mitigating the effects of oxidative stress on neurodegenerative disorders.

Synthesis Reference(s)

Tetrahedron, 48, p. 8677, 1992 DOI: 10.1016/S0040-4020(01)89443-6

Biochem/physiol Actions

Product does not compete with ATP.

Purification Methods

Crystallise PBN from hexane. It is a free radical trap. [cf Janzen Methods Enzymology 105 188 1984, Beilstein 7 IV 519.]

InChI:InChI=1/C11H15NO/c1-11(2,3)12(13)9-10-7-5-4-6-8-10/h4-9H,1-3H3

Upstream product

• 3585-81-7 2-tert-butyl-3-phenyloxaziridine 
• 6852-58-0 (E)-N-benzylidene-2-methylpropan-2-amine 
• 917-95-3 t-butylnitrite 
• 27081-10-3 tropylium tetrafluoroborate 
• 16649-50-6 N-tert-Butylhydroxylamine 
• 13909-34-7 N-benzylidenephenylsulfonamide 
• 100-68-5 methyl-phenyl-thioether 
• 622-78-6 Benzyl isothiocyanate 
• 132413-50-4 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl isothiocyanate 
• 57-06-7 N-allyl isothiocyanate 
• 1122-82-3 isothiocyanatocyclohexane 
• 140134-19-6 N-tert-Butyl-N-(nitrooxy-phenyl-methyl)-hydroxylamine 
• 57497-39-9 N-tertbutylhydroxylamine hydrochloride 
• 100-52-7 benzaldehyde 

Downstream Products

• 61015-94-9 N-(tert-butyl)-N-(2-methyl-1-phenylpropyl)-N-oxyl 
• 72995-56-3 4-benzyl-2-tert-butyl-3-phenyl-[1,2,4]oxadiazolidine-5-thione 
• 50506-95-1 2-tert-butyl-3,4-diphenyl-[1,2,4]oxadiazolidine-5-thione 
• 35105-50-1 (2-tert-butyl-3,4-diphenyl-[1,2,4]oxadiazolidin-5-ylidene)-phenyl-amine 
• 72995-55-2 2-tert-butyl-4-(4-nitro-phenyl)-3-phenyl-[1,2,4]oxadiazolidine-5-thione 
• 34234-86-1 α-Methoxybenzyl-tert-butyl-nitroxyl-Radikal 
• 34280-33-6 methanol adduct of α-phenyl-N-t-butylnitrone 
• 72023-85-9 C₁₄H₂₂NO₂ 
• 21999-41-7 C₁₅H₂₄NO 
• 35822-90-3 benzoyl-tert-butylnitroxyl radical 
• 39058-87-2 C₁₅H₂₄NO₂ 
• 67036-25-3 C₁₅H₂₄NO₃ 
• 78935-76-9 C₂₀H₂₈ClNOSi 
• 78935-71-4 C₂₀H₂₇Cl₂NOSi 

Relevant articles and documents

Control of methyl methacrylate radical polymerization via Enhanced Spin Capturing Polymerization (ESCP)

The nitrone mediated polymerization of methyl methacrylate (MMA) via the enhanced (termination) spin capturing polymerization (ESCP) process is made possible via the addition of small amounts of styrene (between 5 and 10 vol.%) to the reaction mixture. Efficient control over the molecular weight between 7000 and 57,000 g mol-1 (at 60 °C) yields macromolecules that feature a mid-chain alkoxyamine functionality and are rich in methyl methacrylate. The collated kinetic and molecular weight data allow for a deduction of the spin capturing constant, CSC, in the range between 0.15 and 0.30. During the ESCP process, the number average molecular weight, Mn, of the formed mid-chain functional polymer is constant up to high monomer to polymer conversions (i.e. 80%). The high degree of alkoxyamine mid-chain functionality present in the generated polymeric material is evidenced via a subsequent nitroxide-mediated polymerization process employing the formed ESCP polymer, indicating a chain extension from 37,700 to 118,000 g mol-1 with a concomitant reduction in polydispersity (from 2.3 to 1.5).

Weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis

The selective rearrangement of oxaziridines to amidesviaa single electron transfer (SET) pathway is unexplored. In this study, we present a weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis. The developed method shows excellent functional group tolerance with a broad substrate scope and good to excellent yields. Furthermore, control experiments and density functional theory (DFT) calculations are performed to gain insight into the reactivity and selectivity.

S -Tetrazine: Robust and Green Photoorganocatalyst for Aerobic Oxidation of N,N-Disubstituted Hydroxylamines to Nitrones

Efficient photocatalytic aerobic oxidative dehydrogenation reactions of N,N-disubstituted hydroxylamines to nitrones were developed with an in situ generated photocatalyst based on commercially available 3,6-dichlorotetrazine. This process affords a wide range of nitrones in high yields under mild conditions. In addition, an oxidative (3+3) cycloaddition between an oxyallyl cation precursor and a hydroxylamine was also developed.