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

Chemical Properties

white to light beige fine crystalline powder

Uses

Different sources of media describe the Uses of 3376-24-7 differently. You can refer to the following data:
1. Spin trap reagent for carbon- or oxygen- or nitrogen-centered free radicals.
2. N-tert-Butyl-a-phenylnitrone is a commonly-used free radical trap. It contains radical scavenging activity and an ability to inhibit Cox-2 (cyclooxygenase-2). N-tert-Butyl-a-phenylnitrone is an antioxidant that has been shown to act as a protective agent in several experimental models of neurodegenerative disorders. N-tert-Butyl-a-phenylnitrone inhibits lipid peroxidation in rat liver microsomes. It also prevents the induction of inducible nitric oxide synthase (iNOS) by reactive oxygen species.
3. N-tert-Butyl-α-phenylnitrone has been used:as a component of Dneasy Blood&Tissue buffer to preserve the oxidized state of DNA extracted from human non-tumorigenic epithelial breast (MCF10A) cellsas a free radical scavenger of reactive oxygen species (ROS) in microglial (MG) cell linesto attenuate fibroblast senescence in unstable oral squamous cell carcinomas (GU-OSCC)

Synthesis Reference(s)

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

General Description

Most commonly-used free radical trap. An antioxidant that has been shown to act as a protective agent in several experimental models of neurodegenerative disorders. Inhibits lipid peroxidation in rat liver microsomes. Also prevents the induction of inducible nitric oxide synthase (iNOS) by reactive oxygen species.

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

• 16649-50-6 N-tert-Butylhydroxylamine 
• 100-52-7 benzaldehyde 
• 594-70-7 2-Methyl-2-nitropropane 
• 3378-72-1 N-tert-butylbenzylamine 
• 6852-58-0 (E)-N-benzylidene-2-methylpropan-2-amine 
• 57497-39-9 N-tertbutylhydroxylamine hydrochloride 
• 3585-81-7 2-tert-butyl-3-phenyloxaziridine 
• 75-05-8 acetonitrile 
• 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 
• 14152-97-7 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate 

Downstream Products

• 68883-38-5 N-benzyl-N-(tert-butyl)hydroxylamine 
• 6852-58-0 N-benzylidene tert-butylamine 
• 72995-56-3 4-benzyl-2-tert-butyl-3-phenyl-[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 
• 35822-90-3 benzoyl-tert-butylnitroxyl radical 
• 39058-87-2 C₁₅H₂₄NO₂ 
• 67036-25-3 C₁₅H₂₄NO₃ 
• 63711-04-6 C₁₂H₁₅Cl₃NO 
• 63710-78-1 C₁₇H₁₉ClNO 
• 89900-86-7 C₁₇H₁₈Cl₂NO 

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.