3910-55-2

Usage

Functional Groups

Butanamine moiety, substituted benzaldehyde group

Structure

A butanamine group with a benzaldehyde group attached to the nitrogen atom

Usage

Building block in organic synthesis

Applications

Production of pharmaceuticals, agrochemicals, and other fine chemicals

Reactivity

Can undergo a variety of chemical reactions

Reactions

Formation of imines, reductive amination, and other transformations

Importance

Valuable tool in organic chemistry

Versatility

Key component in the synthesis of diverse compounds

Industrial and Commercial Applications

Potential use in various industries due to its reactivity and versatility

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 109-73-9 N-butylamine 
• 7332-00-5 n-butylazide 
• 105-13-5 4-Methoxybenzyl alcohol 
• 3246-78-4 N-(4-methoxybenzylidene)-4-methylaniline 
• 3179-10-0 1-methoxy-4-(2-nitro-vinyl)-benzene 
• 874-90-8 4-methoxybenzonitrile 
• 2393-23-9 4-methoxy-benzylamine 

Downstream Products

• 88818-49-9 1-(4-Methoxyphenyl)-2-nitro-1-buten-3-one 
• 3910-58-5 N-(4-methoxybenzyl)butan-1-amine 
• 4589-09-7 meso-1,2-Bis(4-methoxyphenyl)-N,N'-dibutylethylendiamin 
• 127143-28-6 1-(2-chloro-2-nitroethenyl)-4-methoxybenzene 
• 22013-86-1 1-(2-bromo-2-nitrovinyl)-4-methoxybenzene 
• 141-05-9 Diethyl maleate 
• 105202-49-1 3-Benzoyl-4-(p-methoxyphenyl)-5-isoxazolamine 
• 1019490-45-9 N-butyl-N-[1-(4-methoxyphenyl)propyl]amine 
• 3246-78-4 N-(4-methoxybenzylidene)-4-methylaniline 
• 109-73-9 N-butylamine 

Relevant academic research and scientific papers

[2]Pseudorotaxanes based on naphtho-21-crown-7 and secondary dialkylammonium salts: Remarkably improved association constants among four threaded structures

This research article is focused on the recognition interaction of a new host naphtho-21-crown-7 and four secondary dialkylammonium salts. In acetone, they can form 1:1 host-guest complexes which belong to slow-exchange systems. We also found the differen

Selective Acceptorless Dehydrogenation of Primary Amines to Imines by Core–Shell Cobalt Nanoparticles

Core–shell nanocatalysts are attractive due to their versatility and stability. Here, we describe cobalt nanoparticles encapsulated within graphitic shells prepared via the pyrolysis of a cationic poly-ionic liquid (PIL) with a cobalt(II) chloride anion. The resulting material has a core–shell structure that displays excellent activity and selectivity in the self-dehydrogenation and hetero-dehydrogenation of primary amines to their corresponding imines. Furthermore, the catalyst exhibits excellent activity in the synthesis of secondary imines from substrates with various reducible functional groups (C=C, C≡C and C≡N) and amino acid derivatives.

Tunable Synthesis of α-Amino Boronic Esters from Available Aldehydes and Amines through Sequential One-Pot Dehydration and Copper-Catalyzed Borylacylation

Copper-catalyzed multicomponent borylacylation of imines with acid chlorides and bis(pinacolato)diboron was developed for the preparation of synthetically useful and pharmacologically relevant α-amino boronic acid derivatives. Starting from a range of acid chlorides and imines with aryl, heteroaryl, and alkyl substituents, most of these ligand-free reactions proceeded smoothly at room temperature in moderate to good yields. Furthermore, a facile and convenient one-pot, multistep access to the direct synthesis of α-amino boronic acid derivatives from available aldehydes and amines was also developed.

Au nanoparticle-immobilized L-cysteine-paired porous ionic copolymer as an efficient catalyst for additive-free oxidative coupling of alcohols and amines

Herein, an L-cysteine-paired ionic copolymer (DVB-[MimLcy]n) with mesoporosity was prepared by free radical copolymerization of divinylbenzene (DVB) and imidazolium ionic liquids (ILs), followed by anion-exchange with L-cysteine. Because of the rich functional groups of –NH2, –SH, and –COO– and the porous framework, the DVB-[MimLcy]3 was revealed to be an ideal stabilizer for metal nanoparticles (NPs). Highly uniform dispersed small Au NPs (2–3 nm) immobilized on DVB-[MimLcy]3 (Aua/DVB-[MimLcy]3) can act as an efficient heterogeneous catalyst for additive-free synthesis of imines through coupling of a broad range of alcohols and organic amines and can be easily recovered and steadily reused several times.

Synthesis of Secondary Aldimines from the Hydrogenative Cross-Coupling of Nitriles and Amines over Al2O3-Supported Ni Catalysts

A heterogeneous Ni catalyst was discovered to be active in the synthesis of secondary cross-imines via hydrogenative coupling of nitriles and amines. The mesoporous Al2O3-supported Ni nanoparticles (abbreviated as Ni/m-Al2O3-600, where 600 represents the reduction temperature) were active in hydrogenative coupling of nitriles and amines reaction at 80 °C and 1 bar H2, affording corresponding cross-imines with yields in the range 64.1-98.1%. Density functional theory calculations reveal the hydrogenation of benzonitrile (PhCN) to benzylamine (PhCH2NH2) has higher activation energy than that for hydrogenative cross-coupling of PhCN and RNH2 on the Ni/m-Al2O3-600 catalyst, suggesting the latter reaction is more favorable. The theoretical calculations are in good agreement with our experimental results.

Direct synthesis of imines by 9-azabicyclo-[3,3,1]nonan-N-oxyl/KOH-catalyzed aerobic oxidative coupling of alcohols and amines

A simple and efficient method for preparation of imines by the oxidative coupling of benzyl alcohols with aromatic amines or aliphatic amines was developed. The reaction was catalyzed by 9-azabicyclo[3.3.1]nonan-N-oxyl (ABNO)/KOH with air as the economic and green oxidant. Under the optimal reaction conditions, a variety of imines were obtained in 80%-96% isolated yields.

Mechanistic Studies on the Michael Addition of Amines and Hydrazines to Nitrostyrenes: Nitroalkane Elimination via a Retro-aza-Henry-Type Process

In this article we report on the mechanistic studies of the Michael addition of amines and hydrazines to nitrostyrenes. Under the present conditions, the corresponding N-alkyl/aryl substituted benzyl imines and N-methyl/phenyl substituted benzyl hydrazones were observed via a retro-aza-Henry-type process. By combining organic synthesis and characterization experiments with computational chemistry calculations, we reveal that this reaction proceeds via a protic solvent-mediated mechanism. Experiments in deuterated methanol CD3OD reveal the synthesis and isolation of the corresponding deuterated intermediated Michael adduct, results that support the proposed slovent-mediated pathway. From the synthetic point of view, the reaction occurs under mild, noncatalytic conditions and can be used as a useful platform to yield the biologically important N-methyl pyrazoles in a one-pot manner, simple starting with the corresponding nitrostyrenes and the methylhydrazine.

Method for preparing imine compound from alcohol and amine through catalytic oxidation

The invention discloses a method for preparing an imine compound from alcohol and amine through catalytic oxidation. According to the method, an alcohol compound and an amine compound are used as reaction substrates, and a feeding mol ratio of the alcohol compound to the amine compound is 100: 100-60; 9-azabicyclo[3.3.1]nonane N-oxyl free radical is used as a catalyst, potassium hydroxide is used as an auxiliary agent, and a feeding mol ratio of the amine compound to the 9-azabicyclo[3.3.1]nonane N-oxyl free radical to potassium hydroxide is 100: 1-6: 10-50; air is used as an oxidizing agent, the reaction substrates are added into an organic solvent, and the mass of the used organic solvent is 2.5 to 5 times of the reaction substrate the amine compound; and a reaction is carried out at normal pressure at a temperature of 70 to 110 DEG C for 2 to 12 h, and aftertreatment is carried out after completion of the reaction so as to obtain the imine compound. The method provided by the invention is simple and safe to operate, reduces environmental cost due to usage of clean oxygen as the oxidizing agent and prevents the problem of transition-metal pollution by discarding usage of any transition-metal catalyst.

Asymmetric induction in the addition of enantiomerically pure H-phosphinate to chiral aldimines: diastereoselective generation of α-amino phosphinates with P,C-stereogenic centers

α-Amino phosphinates with P,C-stereogenic centers were prepared from a P-retained addition of (RP)-(?)-menthyl H-phenylphosphinate to (R)-aldimines with up to 86:14 dr under catalyst and solvent free condition at ambient temperature; the single

Effective catalysis of imine metathesis by means of fast transiminations between aromatic-aromatic or aromatic-aliphatic amines

This paper reports on a quantitative investigation of rates of amine-imine exchange reactions of primary amines with their benzylidene derivatives in organic solvents at room temperature. Exchange reactions involving aromatic-aromatic or aromatic-aliphati