45579-94-0

Upstream product

• 100-46-9 benzylamine 
• 622-79-7 benzyl azide 
• 100-47-0 benzonitrile 

Downstream Products

• 82-45-1 1-amino-9,10-anthracenedione 
• 780-25-6 N-benzylidene benzylamine 
• 100-47-0 benzonitrile 
• 1577258-77-5 C₁₉H₂₇⁽²⁾H₂N₂O₂P 
• 1421865-23-7 C₁₁H₇⁽²⁾H₈NO 

Relevant academic research and scientific papers

Gold(I)-catalyzed selective heterocyclization of propargylic thioureas: Mechanistic study of competitive gold-activation mode

A new selective gold(I)-catalyzed intramolecular heterocyclization of propargylic thioureas has been developed, efficiently affording two kinds of cycloadducts in moderate to excellent yields with a broad substrate scope. Further mechanistic investigation

Switch in Catalyst State: Single Bifunctional Bi-state Catalyst for Two Different Reactions

Disclosed here is a molecular switch which responds to acid-base stimuli and serves as a bi-state catalyst for two different reactions. The two states of the switch serve as a highly active and poorly active catalyst for two catalytic reactions (namely a hydrogenation and a dehydrogenative coupling) but in a complementary manner. The system was used in an assisted tandem catalysis set-up involving dehydrogenative coupling of an amine and then hydrogenation of the resulting imine product by switching between the respective states of the catalyst.

Novel ruthenium-terpyridyl complex for direct oxidation of amines to nitriles

High catalytic activity and selectivity has been demonstrated for the oxidation of both aliphatic and aromatic amines to nitriles under benign conditions with dioxygen or air using the Ru2Cl4(az-tpy) 2 complex. The conversion was found to be strongly influenced by the alkyl chain length of the reactant with shorter chain amines found to have lower conversions than those with longer chains. Importantly, by using the ruthenium terpyridine complex functionalized with azulenyl moiety at the 4 position of central pyridine core provided a much higher reactivity catalyst compared with a series of ruthenium terpyridine-based ligand complexes reported. Mechanistic studies using deuterated benzylamine demonstrated the importance of RuOH in this reaction.

Nucleophilic substitution reactions of N-methyl α-bromoacetanilides with benzylamines in dimethyl sulfoxide

Kinetic studies of the reactions of N-methyl-Y-a-bromoacetanilides with substituted X-benzylamines have been carried out in dimethyl sulfoxide at 25.0 °C. The Hammett plots for substituent X variations in the nucleophiles (log kN vs σX) are slightly bipha

Straightforward carbamoylation of nucleophilic compounds employing organic azides, phosphines, and aqueous trialkylammonium hydrogen carbonate

In the presence of aqueous trialkylammonium hydrogen carbonate, the Staudinger reaction leads to the intermediate formation of the corresponding isocyanate, which, in turn, reacts further with a nucleophilic reagent also present in the mixture and results in carbamoylation with good yield. On the basis of this reaction a practical carbamoylation procedure was devised and a comparative study on suitability of different solvents and phosphorus (III) derivatives for carbamoylation reaction was conducted. The versatility of the method was demonstrated by examples with different classes of nucleophilic compounds that included the aminomethyl resin and natural compounds that display poor solubility in organic solvents.

Kinetics and mechanism of aminolysis of aryl cyclobutane-carboxylates in acetonitrile

The aminolysis of Z-aryl cyclobutanecarboxylates (II) with X-benzylamines is investigated in acetonitrile at 55.0 °C. The rates are uniformly greater by 2.2 times than the corresponding rates of aryl cyclopropanecarboxylates (III). All the selectivity par

Correlation Analysis of Reactivity in the Addition of Substituted Benzylamines to α-Cyano-4-nitrostilbene

The kinetics of addition of a number of ortho-, meta- and para-substituted benzylamines to α-cyano-4-nitrostilbene (CNS) in acetonitrile have been studied.The reaction is first order with respect to CNS.The order with respect to the amine is more than one

Model studies of topaquinone-dependent amine oxidases. 2. Characterization of reaction intermediates and mechanism

The reaction of 2-hydroxy-5-tert-butyl-1,4-benzoquinone (1a) and benzylamine in acetonitrile was studied under anaerobic conditions. Addition of benzylamine to the quinone 1a solution generates the anionic form of the quinone (λ(max) at 492 nm), followed by the formation of the product Schiff base 11 with λ(max) at 368 nm and the aminoresorcinol 13 with λ(max) at 304 nm. The rapid dissociation of the 2-hydroxyl proton was confirmed by the isolation of the amine salt 5a in the reaction of tert-butylamine and 1a. The substrate Schiff base 6a was not spectrally detected due to its lower extinction coefficient and rapid conversion to the product Schiff base 11. However, when α-methylbenzylamine was employed as a substrate, the formation of the substrate Schiff base 7 was detected by 1H NMR and UV-vis spectroscopy. Cyclohexylamine, n-propylamine, and ammonia also gave the substrate Schiff bases 8, 9, and 10, respectively. Both the steric bulk and the acidity of the C1 proton of the substrate are found to be factors controlling the further reaction (C1 proton abstraction). Detailed structural analysis of the substrate Schiff base was performed on 8 by 2D NMR spectroscopy, showing that 8 is in its amine salt form and has undergone nucleotophilic addition at C1, the carbonyl carbon next to the 2-hydroxyl group. UV-vis spectroscopy supports the view that 8 is not a solvent-separated ion pair (λ(max) at 454 nm) but an intimate ion pair (λ(max) 352 nm) in CH3CN. The latter λ(max) value is very similar to λ(max) observed for the Schiff base complex seen in bovine serum amine oxidase and different from a Schiff base complex with 4-methoxy-5-tert-butyl-1,2-benzoquinone 14. The product Schiff base 11 was prepared by the reaction of the hydrochloride salt of the aminoresorcinol 13 and benzaldehyde. It has an ε value 10 times larger than that of the substrate Schiff base (7, 8, or 9) at 368 nm. Treatment of 11 with benzylamine yielded the aminoresorcinol 13 and the product, N-benzylidenebenzylamine (PhCH = NCH2Ph). Comparison of these results to catalytic properties of the copper amine oxidases provides support for an aminotransferase mechanism from a Schiff base of topa in a localized p-quinone form.

Kinetics and product studies on Ullmann amination of 1-halogenoanthraquinones catalysed by copper(I)salts in acetonitrile solution

The kinetics and products of reactions of some primary amines (RNH2) with 1-halogenoanthraquininone (AQX) promoted by copper salts, particularly tetrakis(acetonitrile)copper(I) tetrafluoroborate, have been investigated in acetonitrile solution at 70 deg C.Provided that oxygen does not come into contact with solutions of the copper(I) salt and amine, the kinetics of the reactions have the simple form v = k, and the products consist almost entirely of the aminated anthraquinone, AQNHR, and dehalogenated material, AQH, their ratio being directly proportional to .The reaction rate is dependent on the identity of the departing halogen X, decreasing in the sequence I > Br > Cl, but the product ratio is little affected.N-Deuteration of the reactant amine gives rise to a small kinetic isotope effect, but the product ratio is unaffected.Conversely deutearation on the α-carbon atom of the amine has little kinetic effect but leads to a four-fold increase in the ratio of aminated to dehalogenated product.The observations are interpreted in terms of (i) formation of a copper(I)-amine complex, (II) activation of this species for attack on AQX by proton abstraction from an amine ligand by a free molecule (stepwise or concerted), and (iii) generation of an arylcopper(III) intermediate which is partitioned between formation of AQNHR by attack of an externel amine molecule and formation of AQH by an intramolecular process involving hydrogen transfer from the α-carbon atom in the amine ligand generated in (ii).Exposure of the initial copper(I)-amine complex to oxygen leads to a new complex, itself capable of reacting with AQX, which on prolonged incubation at 70 deg C in the presence of an excess of amine is transformed back to its original state.

Formation and Isomerization of 2-Azaallyllithium Reagents in Deprotonations of N-Benzyl Ketimines Containing α-Protons

Deprotonation of the N-benzylimine of 3-pentanone by lithium diisopropylamide (LDA) in tetrahydrofuran occurs at the benzylic position to give a 2-azaallyllithium reagent in high yield.On standing, the 2-azaallyllithium reagent isomerizes to a 1-azaallyllithium reagent.The N-benzylimine of 2-butanone can be similarly deprotonated by LDA at the benzylic position in competition with deprotonation at the α-positions to give a 2-azaallyllithium reagent in up to 22percent yield.The N-benzylimine of acetone is not appreciably deprotonated at the benzylic position by LDA.Kinetic studies of the isomerization of 2-azaallyl- to 1-azaallyllithium reagent from the 3-pentanone imine suggest that this reaction proceeds by a protonation-deprotonation sequence.