35822-90-3

Basic information

• Product Name: [benzoyl(tert-butyl)amino]oxidanyl
• CAS NO: 35822-90-3
• Molecular Formula: C₁₁H₁₄NO₂
• Molecular Weight: 192.2344
• Mol File: 35822-90-3.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: [benzoyl(tert-butyl)amino]oxidanyl(CAS DataBase Reference)
• NIST Chemistry Reference: [benzoyl(tert-butyl)amino]oxidanyl(35822-90-3)
• EPA Substance Registry System: [benzoyl(tert-butyl)amino]oxidanyl(35822-90-3)

Safety Data

• Hazardous Substances Data: 35822-90-3(Hazardous Substances Data)

Upstream product

• 7419-56-9 N-hydroxy-N-(1,1-dimethylethyl)benzamide 
• 75-91-2 tert.-butylhydroperoxide 
• 1876-22-8 di-tert-butyl diperoxyoxalate 
• 3376-24-7 N-tert-butyl-α-phenylnitrone 
• 917-95-3 t-butylnitrite 
• 7269-35-4 S-(n-butyl) benzothioate 
• 884-09-3 phenyl thiobenzoate 
• 1001-62-3 bis(methanesulfonyl)peroxide 
• 45985-26-0 4-oxo-2,2,6,6-tetramethylpiperidin-oxyl 
• 3376-24-7 (Z)-N-benzylidene-2-methylpropan-2-amine oxide 
• 88867-65-6 N-(2,2-Dimethyl-propionyloxy)-N-phenyl-acetamide 
• 88867-64-5 N-(pivaloyloxy)-p-acetotoluidide 
• 88887-33-6 N-(2,2-Dimethyl-propionyloxy)-N-(4-nitro-phenyl)-acetamide 
• 142764-21-4 Dioxybis<(n-butoxy)phenylphosphane oxide> 

Downstream Products

• 73096-12-5 N-Benzoyl-O-(1-ethoxyethyl)-N-tert-butyl-hydroxylamin 
• 73096-11-4 C₂₄H₂₅N₃O₂ 
• 128174-94-7 N-benzoyl-N-t-butyl-O-(1,3-dithian-2-yl)hydroxylamine 
• 128174-95-8 N-benzoyl-N-t-butyl-O-(1,3,5,2,4-trithiadazin-6-yl)hydroxylamine 

Relevant articles and documents

ESR Spin-Trapping Study of the Radicals Produced in NOx/Olefin Reactions. A Mechanism for the Production of the Apparently Long-Lived Radicals in Gas-Phase Cigarette Smoke.

Gas-phase cigarette smoke contains high concentrations of both oxygen- and carbon-centered free radicals.We have detected these radicals using several variations of the electron spin resonance (ESR) spin-trapping technique, including the use of spin traps in the solid state, to show that the radicals are trapped directly from the gas phase.These gas-phase radicals can still be trapped from gas-phase smoke that is more than 5 min old, a result that is clearly inconsistent with the highly reactive nature of oxygen- and carbon-centered radicals.To rationalize this apparent paradox, we hypothesize that free radicals are continuously produced and destroyed in cigarette smoke and exist in a steady state.We suggest that one mechanism by which radicals can be formed involves the slow oxidation of the relatively unreactive nitric oxide (which acts as a "radical reservoir") to the much more reactive nitrogen dioxide.Nitrogen dioxide can then react with a number of the species that are present in smoke to produce the radicals that we detect.As a model, we have studied the reactions of NO/air mixtures with unsaturated hydrocarbons.Isoprene is one of the most abundant species in smoke and is known to be very reactive toward NO2; therefore we have studied the nature of the radicals that can be spin trapped from gaseous mixtures of NO, isoprene, and air.We find that the NO/air/isoprene model system gives essentially the same types of radicals (oxygen and carbon centered) as does cigarette smoke.We have also studied the gas-phase reactions of NO2 with several small olefins and 1,3-butadiene and find evidence for peroxyl radical intermediates.In solution, NO2 reacts with isoprene much faster than it does with the spin-trap phenyl-tert-butylnitrone (PBN).We find that NO2 oxidizes PBN to benzoyl tert-butyl nitroxide and propose a mechanism for this reaction.

Titanium tetra-tert-butoxide-tert-butyl hydroperoxide oxidizing system: Physicochemical and chemical aspects

The reaction of titanium tetra-tert-butoxide with tert-butyl hydroperoxide (1: 2) (C6H6, 20 C) involves the steps of formation of the titanium-containing peroxide (t-BuO)3TiOOBu-t and peroxytrioxide (t-BuO)3TiOOOBu-t. The latter decomposes with the release of oxygen, often in the singlet form, and also homolytically with cleavage of both peroxy bonds. The corresponding alkoxy and peroxy radicals were identified by ESR using spin traps. The title system oxidizes organic substrates under mild conditions. Depending on the substrate structure, the active oxidant species can be titanium-containing peroxide, peroxytrioxide, and oxygen generated by the system.

Fluoro spin adducts and their modes of formation

The reactions of two fluorinating reagents, XeF2 and N-fluorodibenzenesulfonamide [(PhSO2)2N-F], with several spin traps have been investigated. In dichloromethane, the strong oxidant XeF2 cleanly gives fluoro spin adducts with N-tert-butyl-α-phenylnitrone (PBN) or 5,5-dimethyl-1-pyrroline 1-oxide (DMPO) according to a mechanism mediated by the radical cation of the spin trap. In both cases, further fluorination takes place with replacement of the a hydrogen by fluorine. The much weaker oxidant (PhSO2)2N-F reacts with PBN or DMPO in dichloromethane giving both the fluoro adduct and an adduct formally derived from an N-centred radical, assigned the structure of PhSO2N(F)-PBN? or (PhSO2)2N-DMPO?, respectively. This type of reaction proceeds by a version of the Forrester-Hepburn mechanism, in which an acid HA, in this case HF, initially adds to the nitrone function to give a hydroxylamine derivative which is oxidized by (PhSO2)N-F giving the fluoro spin adduct, a proton and the highly labile radical anion (PhSO2)2N-F?-. By decomposition of the latter to PhSO2(F)N- and PhSO2?, conditions are set up for propagation of the reaction by a new molecule of HA [now PhSO2(F)NH] and thus formation of the PhSO2(F)N spin adduct.