52790-65-5

Upstream product

• 584-48-5 2,4-dinitrobromobenzene 
• 111-26-2 hexan-1-amine 
• 13181-75-4 O-(2,4-dinitrophenyl) cyclohexanone oxime 
• 13181-14-1 1-phenylethan-1-one O-(2,4-dinitrophenyl) oxime 
• 17188-67-9 diphenylmethanone O-(2,4-dinitrophenyl)oxime 
• 115806-86-5 O-(2,4-dinitrophenyl)-4'-bromobenzophenone oxime 
• 75-04-7 ethylamine 
• 109-73-9 N-butylamine 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 17188-66-8 O-(2,4-dinitrophenyl)-p,p'-dichlorobenzophenone oxime 
• 173416-64-3 O-(2,4-dinitrophenyl)-p,p'-difluorobenzophenone oxime 
• 173416-65-4 O-(2,4-dinitrophenyl)-p,p'-dimethoxybenzophenone oxime 
• 17188-68-0 O-(2,4-dinitrophenyl)-p-chlorobenzophenone oxime 
• 99-65-0 meta-dinitrobenzene 

Relevant academic research and scientific papers

Reaction of n-Hexylamine with 2,4-Dinitrochlorobenzene in Microemulsions

Reaction of n-hexylamine with 2,4-dinitrochlorobenzene (DNC) is faster in microemulsions of n-octane, n-hexylamine, and cetyltrimethylammonium bromide (CTABr) than in water.The first-order rate constants, kψ, for reaction in the absence of surf

Pd(OAc)2-catalyzed dinitration reaction of aromatic amines

Taking advantage of Pd(OAc)2-catalyzed dinitration reactions with Bi(NO3)3·5H2O in trifluoroethanol (TFE) and trifluoroacetic acid (TFA), we have developed an efficient and practical method for the synthesis of secondary dinitro-aromatic amines. The products could be applied to the preparation of 5-amine-N-methyl-benzimidazolone, the azo-dyes, economic advantages. The method has also been expanded to the dinitration reaction of some tertiary aromatic amines.

Electrochemical synthesis of nitroanilines

Alkylamines and amides are readily prepared by nucleophilic aromatic substitution of hydrogen in nitroarenes by electrochemical oxidation. Useful yields (15-85%) are achieved in a simple direct and regioselective amination process. The synthetic method has been examined in the absence and presence of external bases, used to promote the first step of the nucleophilic aromatic substitution reaction, i.e. the nucleophilic attack. In both cases, good results were obtained. The unreacted starting material can easily be recovered at the end of the electrochemical oxidation process. This new method represents an environmentally favourable route to amino- and amido-substituted nitroaromatic compounds.

Direct formation of aromatic C-N bonds. Regioselective amination of m- dinitrobenzene via fluoride promoted nucleophilic aromatic photosubstitution for hydrogen

Useful yields are achieved in the regioselective direct formation of anilines and aromatic amides through hydrogen nucleophilic aromatic photosubstitution of m-dinitrobenzene with primary amines and amides, promoted by fluoride anion.

Aromatic nucleophilic substitution reactions of O-aryl oximes with piperidine and hexylamine in cyclohexane

A detailed study of piperidinolysis and hexylaminolysis of O-(2,4-dinitrophenyl) benzophenone oxime, O-(2,4-dinitrophenyl)-p-chlorobenzophenone oxime and O-(2,4-dmitrophenyl)-p-bromobenzo-phenone oxime in cyclohexane at different temperatures has been undertaken. The piperidinolysis reactions show a third order dependence on amine and inverse temperature effect. The analysis of data indicates that the reactions proceed through two routes; the rate of first route increases and of the second route decreases with temperature. The overall rate kA shows inverse temperature effect due to predominating effect of the second route. The results support the Jack Hirst's concept of reaction mechanism in nonpolar solvents. In contrast to piperidinolysis, n-hexylaminolysis reactions show only a second order dependence on amine which has been explained to be due to lesser stability of hydrogen bonded homoconjugate acid BH+B involving long chain hexylamine molecules.

Primary alkyl aminolysis of O-(2,4-dinitrophenyl)-p,p'-disubstituted benzophenone oximes in benzene

The reaction of three O-aryl oximes ((C6H4X)2C=N-O-C6H3(NO2)2; X=Cl-, F-, CH3O-) with three primary amines (n-butylamine, n-hexylamine and n-dodecylamine) have been studied at different temperatures (20-40 deg C) in benzene.The aminolysis reaction have been found to be base-catalysed with an uncatalytic step and second order in amine.The occurrence of uncatalytic route has been explained due to intramolecular hydrogen bonding of ammonium proton to the oxygen of leaving group which finds support in the low energy of activation observed.The reaction rates decrease in the order BuNH2>HexNH2>DodNH2 which has been explained in the light of steric hindrance.

Nucleophilic Aromatic Substitution in Microemulsions Stabilized by Chemodegradable Surfactants

Systematic synthetic studies have been performed for the reaction of 2,4-dinitrochlorobenzene (DNCB) with hydroxide, iodide and aryl (phenyl, p-cresyl) oxide ions in oil-in-water microemulsions at 50 deg C.The n-octane-in-water microemulsion systems are stabilized by a chemodegradable trimethylammonium bromide (I) and 1-butanol as cosurfactant.A successful preparative approach has been also elaborated for the reaction of DNCB with n-hexylamine in microemulsion of surfactant I where the amine acts as a reagent and a cosurfactant.In all the studied systems the products have been isolated from the microemulsion medium in approx. 85-95percent yield without unfavourable processes as foaming and emulsification. Key words: micellar catalysis, nucleophilic aromatic substitution, chemodegradable surfactants

Aromatic Nucleophilic Substitution Reactions of Oxime Ethers with Aliphatic Primary and Secondary Amines in Benzene

Reactions of various oxime ethers with the primary alkylamines propyl-, butyl-, pentyl-, and hexylamine and with pyrrolidine, a secondary alkyl amine, have been studied in benzene at 35 +/- 0.1 deg C.These reactions have all been found to be wholly base catalysed.Some reactions, especially those involving strong nucleophiles and substrates with poor leaving groups , exhibit a third-order dependence on amine concentration which has been explained on the basis of a cyclic transition-state mechanism.These reactions also show an inverse-temperature effect. Reactions with substrates which have good leaving groups and weaker nucleophiles show a second-order dependence on amine concentration.These reactions show normal temperature effects with low energy of activation.This low energy of activation and high negative entropy of activation support the cyclic transition-state mechanism invoked to explain these data.

Aminolysis of Oxime Ethers in Protic and Aprotic Solvents

Reactions of oxime ethers with the primary amines, n-propyl-, n-butyl-, n-pentyl-, and n-hexylamine in DMSO, DMF, and MeCN are strongly catalysed by general bases.The observed second-order rate constants (kA) exhibit a curvilinear dependence on amine concentration leaving a positive intercept.The reactions of piperidine in DMSO follow a wholly catalysed pathway.A plot of kA versus is linear and passes through the origin.No base catalysis is observed for the reactions of n-butylamine in methanol and 1:1 (v/v) methanol-acetonitrile.The participation of the hydrogen- bond donor solvent molecule in the intermediate may account for absence of base catalysis in these solvents.

KINETIC STUDIES AND MICELLAR EFFECT ON THE AMINOLYSIS OF CERTAIN O-ARYL OXIMES

Rate constants for the aminolysis of a few O-aryl oximes with several primary alkyl amines, CH3NH2-------C6H12NH2 in 1:1 water-acetonitrile are reported.Reactions of methylamine with substrates possessing poor nucleofugues are very weakly sensitive to base catalysis while reactions of higher amines are not.Slightly higher rate of long chain amine may be considered as a consequence of hydrophobic interaction.Cationic micelles of cetyltrimethyl ammonium bromide enhance the rate.Magnitude of micellar catalysis increases towards higher amines.