98326-78-4

Upstream product

• 107829-09-4 N-(3-nitrophenyl)butyramine 
• 645-00-1 m-iodonitrobenzene 
• 109-73-9 N-butylamine 
• 15676-66-1 tri-n-butylindium 
• 16937-12-5 4-nitro-N-(3-nitrophenyl)benzenesulfonamide 
• 99-09-2 3-nitro-aniline 
• 129882-02-6 N-<1-(benzotriazol-1-yl)butyl>-3-nitroaniline 

Downstream Products

• 129882-03-7 N-butyl-N-<(benzotriazol-1-yl)methyl>-3-nitroaniline 
• 129882-05-9 N-butyl-N-phenethyl-3-nitroaniline 
• 123-72-8 butyraldehyde 
• 99-09-2 3-nitro-aniline 
• 107829-09-4 N-(3-nitrophenyl)butyramine 

Relevant academic research and scientific papers

Chemoselective Deprotection of Sulfonamides under Acidic Conditions: Scope, Sulfonyl Group Migration, and Synthetic Applications

Chemoselective acidic hydrolysis of sulfonamides with trifluoromethanesulfonic acid has been evaluated as a deprotection method and further extended to more complex synthetic applications. In contrast to conventional troublesome sulfonamide hydrolysis, a near-stoichiometric amount of acid was found to be sufficient to bring about efficient deprotection of various neutral or electron-deficient N-arylsulfonamides, whereas electron-rich substrates provided sulfonyl group migration products. The deprotection method developed is fully selective for N-arylsulfonamides, and the possibility to discriminate among various different sulfonamides is demonstrated.

Copper-mediated aryl amination: In situ generation of an active copper(I) species

We have developed novel conditions for copper-mediated aryl amination by using a combination of easy-to-handle and inexpensive Cu(OAc) 2·H2O and phenylhydrazine. Georg Thieme Verlag Stuttgart . New York.

A mild inter- and intramolecular amination of aryl halides with a combination of CuI and CsOAc

A unique combination of CuI and CsOAc was found to catalyze aryl amination under mild conditions. The reaction takes place at room temperature or at 90 °C with broad functional group compatibility. The intramolecular reaction was able to form five-, six-, and seven-membered rings with various protecting groups on the nitrogen atom. The scope of the intermolecular amination, as well as its applications to unsymmetrical N,N′-dialkylated phenylenediamines, was investigated.

Reactions of arenediazonium o-benzenedisulfonimides with aliphatic triorganoindium compounds

The reaction of various arenediazonium o-benzenedisulfonimides with aliphatic triorganoindium compounds is described. Surprisingly, with triethyl- or tributylindium we obtained N-ethyl- or N-butylanilines, respectively. This is the first case in which, at least formally, the reactive site of a diazonium salt is the nitrogen atom directly bonded to the aromatic ring. In contrast, with trimethylindium we obtained only formaldehyde (aryl)hydrazones. In order to explain the difference between trimethyl- and triethylindium we have proposed some reaction mechanisms, supported by detailed density functional (DFT) calculations. The possible role of diazene/hydrazone tautomerism initially assumed was discarded and therefore three mechanisms for the key step (nucleophilic addition of the trialkylindium to the N=N double bond of diazene) were studied. For the favoured mechanism there is a difference in the energy barriers of 2 kcalmol-1 between the reactions with trimethyl- and triethylindium. This difference is explained on the basis of the different C-In bond energies in the two organometallics and it is assumed to be enough to explain their different behaviour under the experimental conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Highly efficient and practical phosphoramidite-copper catalysts for amination of aryl iodides and heteroaryl bromides with alkylamines and N(H)-heterocycles

A highly efficient copper-catalyzed system using phosphoramidite as ligands was applied to N-arylation of alkylamines and N(H)-heterocycles with aryl iodides and heteroaryl bromides. The reactions were carried out in relative mild conditions and good to excellent yields were obtained.

Synthesis and NMR-spectral characterization of N,N-dialkyl-3-nitroanilines, N,N-dialkyl-1,3-benzenediamines and their acyl derivatives

A recently discovered method for the synthesis of N,N-dialkyl-1,3-benzenediamines with two different alkyl groups is shown to be general.This is demonstrated by the synthesis of N-butyl-N-phenethyl-1,3-benzenediamine by the condensation of 3-nitroaniline with phenylacetaldehyde and benzotriazole, reduction of the adduct with sodium borohydride, acylation of the resulting N-phenethyl-3-nitroaniline with butyryl chloride, catalytic reduction of the nitro group by formic acid in the presence of triethylamine and palladium and finally reduction of the butyramide carbonyl group to the butyl substituent by lithium aluminium hydride.Several other routes were less efficient or failed completely.Classical methods for the synthesis of N,N-diethyl-1,3-benzenediamine were reexamined and improved.The recommended procedure involves alkylation of 3-nitroaniline with diethyl sulfate, trapping of N-ethyl-3-nitroaniline (by-product) by benzoylation, distillation of N,N-diethyl-3-nitro-aniline under reduced pressure and reduction of the nitro group by formic acid catalyzed by palladium.

Bis(salicylaldehyde)ethylenedi-iminecobalt(II)-catalysed Oxidation of Aromatic Amins with Oxygen

N-n-Butylanilines undergo N-dealkylation to give a primary amine and butyrylaldehyde by oxidation with oxygen in the presence of bis(salicylaldehyde)ethylenedi-iminecobalt(II) (CoIIsalen) as a catalyst.High conversions are obtained with high catalyst concentrations and low / ratios (r).Inspection of the effect of catalyst and substrate concentrations on initial reaction rates (Vin) shows poor sensitivity to the electronic effect of the nuclear substituent.Some anilines give azo derivatives at a lower rate in the same conditions.