68315-30-0

Usage

Uses

Used in Organic Synthesis:
(Z)-Benzylidene-oxido-tert-butyl-azanium is used as a reagent in organic synthesis for various chemical reactions. Its unique structure and reactivity contribute to the formation of complex organic molecules, making it a valuable component in this field.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (Z)-benzylidene-oxido-tert-butyl-azanium is used as a building block for the synthesis of complex organic molecules with potential medicinal properties. Its versatility and reactivity allow for the development of new drugs and therapeutic compounds.
Used in Agrochemicals:
(Z)-Benzylidene-oxido-tert-butyl-azanium is also utilized in the agrochemical industry, where it serves as a key component in the synthesis of various agrochemical products. Its unique properties enable the creation of effective and targeted solutions for agricultural applications.
Used as a Catalyst:
Furthermore, (Z)-benzylidene-oxido-tert-butyl-azanium is used as a catalyst in certain chemical reactions. Its ability to accelerate and control the rate of these reactions without being consumed makes it an essential tool in the synthesis of various compounds, particularly in the fields of pharmaceuticals, agrochemicals, and materials science.

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 
• 57497-39-9 N-tertbutylhydroxylamine hydrochloride 
• 3585-81-7 2-tert-butyl-3-phenyloxaziridine 
• 75-05-8 acetonitrile 
• 917-95-3 t-butylnitrite 
• 27081-10-3 tropylium tetrafluoroborate 
• 75-64-9 tert-butylamine 
• 100-68-5 methyl-phenyl-thioether 
• 14152-97-7 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate 
• 140134-19-6 N-tert-Butyl-N-(nitrooxy-phenyl-methyl)-hydroxylamine 
• 6852-58-0 N-benzylidene tert-butylamine 

Downstream Products

• 34234-86-1 α-Methoxybenzyl-tert-butyl-nitroxyl-Radikal 
• 34280-33-6 methanol adduct of α-phenyl-N-t-butylnitrone 
• 72023-85-9 C₁₄H₂₂NO₂ 
• 21894-27-9 N-tert-butyl-N-(1-phenylethyl)nitroxide 
• 53544-93-7 2,2,5,5-tetramethyl-4-phenyl-3-azahexane-3-nitroxide 
• 78759-34-9 trans-4-Cyano-5-nitro-trans-3-phenyl-N-tert-butylisoxazolidine 
• 78759-35-0 trans-5-cyano-4-nitro-3-phenyl-N-tert-butylisoxazolidine 
• 73023-54-8 C₁₅H₂₄NO₂ 
• 72023-86-0 C₁₅H₂₄NO₂ 
• 102148-00-5 C₂₄H₃₀N₃O₃ 
• 102147-98-8 C₃₀H₃₄N₃O₃ 
• 102147-99-9 C₃₀H₃₂N₃O₄ 
• 77601-78-6 C₁₉H₃₃N₂O 
• 72023-87-1 C₁₈H₂₂NO₂ 

Relevant academic research and scientific papers

Metal-Free Solvent Promoted Oxidation of Benzylic Secondary Amines to Nitrones with H2O2

An environmentally benign protocol for the generation of nitrones from benzylic secondary amines via catalyst-free oxidation of secondary amines using H2O2 in MeOH or CH3CN is described. This methodology provides a selective access to a variety of C-aryl nitrones in yields of 60 to 93%. Several studies have been performed to shed light on the reaction mechanism and the role of the solvent.

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.

The effect of viscosity on the coupling and hydrogen-abstraction reaction between transient and persistent radicals

The effect of viscosity on the radical termination reaction between a transient radical and a persistent radical undergoing a coupling reaction (Coup) or hydrogen abstraction (Abst) was examined. In a non-viscous solvent, such as benzene (bulk viscosity bulk 99% Coup/Abst selectivity, but Coup/Abst decreased as the viscosity increased (89/11 in PEG400 at 25 °C [bulk = 84 mPa s]). While bulk viscosity is a good parameter to predict the Coup/Abst selectivity in each solvent, microviscosity is the more general parameter. Poly(methyl methacrylate) (PMMA)-end radicals had a more significant viscosity effect than polystyrene (PSt)-end radicals, and the Coup/Abst ratio of the former dropped to 50/50 in highly viscous media (bulk = 3980 mPa s), while the latter maintained high Coup/ Abst selectivity (84/16). These results, together with the low thermal stability of dormant PMMA-TEMPO species compared with that of PSt-TEMPO species, are attributed to the limitation of the nitroxide-mediated radical polymerization of MMA. While both organotellurium and bromine compounds were used as precursors of radicals, the former was superior to the latter for the clean generation of radical species.

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.

Aliphatic nitro compounds chemistry: oximes–nitrones tunable production through directed tandem synthesis

Abstract: Reduction of aliphatic nitro compounds in the presence of aldehydes and dialdehydes for tunable directed synthesis of oximes, nitrones, nitrone–oximes, and dinitrones was reported. The slow and nonselective reduction of aliphatic nitro compounds was directed by condensation of in situ prepared alkylhydroxylamines with aromatic aldehydes. Mononitrones and dinitrones were synthesized at reflux and at 55?°C conditions, respectively, in tetrahydrofuran using SnCl2?2H2O and Na2CO3. It was found that the presence of a catalytic amount of carboxylic acid such as 3-phenylpropanoic acid increases the yield of dinitrones versus nitrone–oxime and dioxime when dialdehydes were used as aldehyde source. Graphical abstract: [Figure not available: see fulltext.].

Accessing benzooxadiazepines: Via formal [4 + 3] cycloadditions of aza- o -quinone methides with nitrones

An unprecedented and efficient [4 + 3] cycloaddition of N-(ortho-chloromethyl)aryl amides with nitrones has been developed. This approach provides easy access to a series of seven-membered benzooxadiazepine derivatives in good to excellent yields (up to 99% yield) under mild reaction conditions.

Light-induced formation of nitroxyl radicals by organic Bi(V) compounds in the presence of 2-methyl-2-nitrosopropane and C-phenyl-N-tert-butylnitrone

The organic bismuth compounds Ph3Bi(O2CCH=CHCH3)2 and Ph3Bi(O2CEt)2 decompose under scattered light in the presence of spin traps (2-methyl-2-nitrosopropane and C-phenyl-N-tert-butylnitrone) in organic solvents (acetonitrile, benzene, toluene) to form adducts of phenyl radicals with the traps.

REGULATORS FOR CONTROLLING LINEAR AND PSEUDO-RING EXPANSION POLYMERIZATION OF VINYL MONOMERS

The invention concerns new regulator compounds for a novel polymerization process for vinyl monomers, which yields polymers with improved control over composition and nearly full to full conservation of architectural integrity up to high conversion. The regulator compounds are defined by according to anyone of the Formulas (1A), (1B), (1C), (1D), (1E), (1F), (1G), (1H) and (1I), wherein R1 stands for an optionally substituted secondary or tertiary alkyl or secondary or tertiary aralkyl; Z1 stands for -CN or a carboxylic acid ester of formula C(O)OR21; Z2 may be chosen from the group of -CN, carboxylic acid, salts of carboxylic acids, carboxylic acid ester, carboxylic acid amides, (hetero)aryl, alkenyl and halogen; R2, R3, R4 and R5 are each independently chosen from the group of H, alkyl, aralkyl, (hetero)aryl, -CN and carboxylic acid ester of formula C(O)OR22; R7 stands for a primary alkyl or primary aralkyl, -CN or hydrogen; Y stands for a bridging group and n is 2, 3, 4, 5 or 6; in case R1 stands for tertiary alkyl or tertiary aralkyl, R6 stands for a primary alkyl or primary aralkyl, -CN or a carboxylic acid ester of formula C(O)OR26; in case R1 stands for a secondary alkyl or secondary aralkyl, R6 stands for a primary or secondary alkyl or primary or secondary aralkyl, -CN, a carboxylic acid ester of formula C(O)OR26 or a phosphonic acid ester of formula P(O)(OR27)2, a (hetero)aryl or an alkenyl; R21, R22, R26 and R27 each independently stand for alkyl or aralkyi having from 1-30 carbon atoms, optionally containing heteroatoms.

Method for preparing nitrone from secondary amine

The invention relates to a method for preparing nitrone from secondary amine. The method comprises the steps of adding 2 mmol of the secondary amine into a reactor, sequentially adding 4-5 mL of water, 0.02-0.03 mmol of tetrabutylammonium bromide, 0.02-0.08 mmol of a catalyst WO3-x and 3-6 mmol of a hydrogen peroxide solution with the concentration being 30-50%, and stirring the mixture for 2-6 hours at the temperature of 25-60 DEG C; or adding 2 mmol of the secondary amine into a reactor, adding 3-5 mL of polar solvent, 0.02-0.08 mmol of a catalyst WO3-x ad 3-6 mmol of a hydrogen peroxide solution with the concentration being 30-50%, and stirring the mixture for 2-6 hours at the temperature of 25-60 DEG C; diluting a mixed solution obtained after a reaction to 15-20 mL, conducting extraction, concentration and column chromatography isolation, and collecting a product. The catalyst adopted in the method is WO3-x nanosheets having oxygen vacancies and is high in catalytic oxidation activity; raw materials of the method are wide in source, the reaction condition is simple, the reaction temperature is low, the nitrone yield is high, and water serves as reaction solvent, so that the whole reaction steps are free of pollution, environmentally friendly and low in cost, high industrial application value is achieved, and in addition, great environmental and social significance is achieved.

Dual Role of Pyrrolidine and Cooperative Pyrrolidine/Pyrrolidinium Effect in Nitrone Formation

The formation of nitrones by direct condensation between equimolecular amounts of N-substituted hydroxylamine hydrochlorides and aromatic or aliphatic aldehydes is efficiently promoted by pyrrolidine in a matter of minutes under very mild conditions in almost quantitative yields after a simple filtration through a short pad of silica gel. According to theoretical, spectroscopic, and experimental studies, this success is due to the ability of pyrrolidine to liberate the hydrochloride of the hydroxylamine and catalyze the reaction via iminium activation ion. Moreover, a cooperative pyrrolidine/pyrrolidinium chloride effect facilitates several steps of the catalytic cycle through proton transfer without hampering the nucleophilicity of the hydroxylamine by protonation.