65145-14-4

Usage

Uses

Used in Chemical Synthesis:
N,N-Dibenzyl-4-bromoaniline is used as a chemical intermediate for the synthesis of more complex compounds. Its unique structure, which includes bromine and benzene rings, makes it a valuable building block in the creation of various organic molecules.
Used in Research Applications:
In the field of chemistry, N,N-dibenzyl-4-bromoaniline is used as a research compound to study its properties and potential applications. Its reactivity and the presence of the bromine atom make it an interesting subject for chemical investigations and the development of new synthetic pathways.
Used in Pharmaceutical Development:
N,N-Dibenzyl-4-bromoaniline may be used as a starting material in the development of new pharmaceutical compounds. Its aromatic and amine characteristics could potentially contribute to the creation of novel drug molecules with specific therapeutic properties.
Used in Material Science:
In material science, N,N-dibenzyl-4-bromoaniline could be employed in the design and synthesis of new materials with unique properties. Its chemical structure may contribute to the development of advanced materials for various applications, such as electronics, coatings, or adhesives.

InChI:InChI=1/C20H18BrN/c21-19-11-13-20(14-12-19)22(15-17-7-3-1-4-8-17)16-18-9-5-2-6-10-18/h1-14H,15-16H2

Upstream product

• 91-73-6 N,N-dibenzylaniline 
• 586-78-7 para-nitrophenyl bromide 
• 100-51-6 benzyl alcohol 
• 98-88-4 benzoyl chloride 
• 70787-27-8 N-(2-bromophenyl)benzamide 
• 615-36-1 2-bromoaniline 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 1075193-04-2 N,N-dibenzyl-2-bromoaniline 
• 780-20-1 N-benzylidene-4-bromoaniline 
• 100-52-7 benzaldehyde 
• 52742-32-2 N,N-dibenzyl-O-benzoylhydroxylamine 
• 106-40-1 4-bromo-aniline 
• 947515-73-3 (4-bromophenyl)[2-(hydroxymethyl)phenyl]dimethylsilane 

Downstream Products

• 62849-48-3 N,N-dibenzyl-4-phenylthioaniline 
• 159191-44-3 [4-(dibenzylamino)phenyl]boronic acid 
• 1227159-94-5 ethyl {1-[4-(dibenzylamino)phenyl]cyclobutyl}acetate 
• 1227159-95-6 2-{1-[4-(dibenzylamino)phenyl]cyclobutyl}ethanol 
• 1227159-96-7 N,N-dibenzyl-4-[1-(2-fluoroethyl)cyclobutyl]aniline 
• 1227160-09-9 {1-[4-(dibenzylamino)phenyl]cyclobutyl}acetic acid 
• 1227160-10-2 2-{1-[4-(dibenzylamino)phenyl]cyclobutyl}-N,N-dimethylacetamide 
• 1221819-62-0 4-(oxetan-3-yl)aniline 
• 52805-39-7 4-(N,N-dibenzylamino)benzonitrile 
• 2879-83-6 N-benzyl-N-(4-bromophenyl)amine 

Relevant academic research and scientific papers

Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C-N Cleavage of N, N-Dibenzylanilines

A visible-light-driven photoredox-catalyzed nonaqueous oxidative C-N cleavage of N,N-dibenzylanilines to 2° amides is reported. Further, we have applied this protocol on 2-(dibenzylamino)benzamide to afford quinazolinones with (NH4)2S2O8 as an additive. Mechanistic studies imply that the reaction might undergo in situ generation of α-amino radical to imine by C-N bond cleavage followed by the addition of superoxide ion to form amides.

N-Benzylation of primary amines using magnetic Fe3O4 nanoparticles functionalized with hexamethylenetetramine as an efficient and recyclable heterogeneous catalyst

Herein we report, a new, simple and mild procedure for N-benzylation and N,N-dibenzylation of anilines through the reaction of aniline derivatives and benzyl bromide at 60 °C in EtOH in the presence of catalytic amounts of magnetic Fe3O4 nanoparticles functionalized with hexamethylenetetramine (Fe3O4?SiO2?Propyl-HMTA). The title compounds were formed in high purity and their structures characterized by spectral analysis. The results also showed that the magnetic nanoparticle catalyst had significant advantages including, simplicity of preparation, heterogeneity, stability and recyclability. Moreover, the catalyst was characterized by various methods, such as FT-IR, SEM, VSM, TEM, TGA and XRD, after the reaction to compare with its structure before reaction.

Pyridazine-3-carboxamide compound and preparation method and application thereof in medicine

The invention relates to a pyridazine-3-carboxamide compound suitable for inhibiting or regulating Janus kinase (JAK), especially tyrosine kinase 2 (TYK2), a preparation method of the pyridazine-3-carboxamide compound and an application of the pyridazine-3-carboxamide compound in medicine. Specifically, the invention relates to a compound represented by a general formula (I) and pharmaceutically acceptable salts thereof, a pharmaceutical composition containing the compound or the pharmaceutically acceptable salts thereof, and a method for treating and/or preventing Janus kinase-mediated related diseases, especially autoimmune diseases, inflammatory diseases and cancer by applying the compound or the pharmaceutically acceptable salts thereof, and a preparation method of the compound or thepharmaceutically acceptable salts thereof. Each substituent of the general formula (I) has the same definition as in the specification.

Copper-catalyzed and additive free decarboxylative trifluoromethylation of aromatic and heteroaromatic iodides

A copper-catalyzed decarboxylative trifluoromethylation of (hetero)aromatic iodides has been developed. Importantly, this new copper-catalyzed reaction operates in the absence of any ligands and metal additives. The protocol shows good functional group tolerance and is compatible with heteroaromatic systems. The reaction proved scalable to a 15 mmol scale with increased yield. Finally, late-stage installation of the trifluoromethyl functionality afforded the N-trifluoroacetamide variant of the antidepressant agent, Prozac, demonstrating the applicability of the developed method.

METHOD FOR PRODUCING ORGANOSILICON COMPOUND, METHOD FOR PRODUCING AMINO ARYL GROUP-CONTAINING ORGANOSILICON COMPOUND AND ORGANOSILICON COMPOUND

PROBLEM TO BE SOLVED: To provide a production method that can efficiently produce an amino aryl group-containing organosilicon compound at low cost. SOLUTION: An organosilicon compound represented by general formula (1) is produced by the following reaction or the like, and a benzyl group is deprotected from an amino group thereof, so that an amino aryl group-containing silicon compound is produced. R1-R4, R7 each represent a hydrogen atom, an alkyl group or an alkoxy group; R 5 and R6 each represent an alkyl group; X is a halogen atom; M is a lithium atom or magnesium halide; n is an integer of 1-4; m is an integer of 1-n. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation

Herein, we report a Ni-catalyzed reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for the use of more challenging aryl electrophiles such as aryl chlorides, tosylates, and triflates. Mechanistic investigations suggest that NaBr plays a role in facilitating oxidative addition with these substrates.

Ruthenium nanoparticle catalyzed selective reductive amination of imine with aldehyde to access tertiary amines

Reductive amination is one of the most frequently used transformations in organic synthesis. Herein, we developed a novel ruthenium nanoparticle embedded ordered mesoporous carbon catalyst (Ru-OMC) and a new hydrosilylation process for the synthesis of tertiary amines. We present a direct reductive amination of imines (CN bond) with aldehydes (CO bond) using hydrosilane as the reducing reagent under mild conditions. Moreover, the Ru-OMC catalysts can be reused for up to 14 runs without noticeably losing activity.

MIL-101(Cr) as a synergistic catalyst for the reduction of imines with trichlorosilane

The development of catalyst based on porous crystalline materials (PCM) constructed from metal ions or clusters and multidentate organic ligands is a topic of great interest. In view of the Lewis acidic and basic properties of PCMs, we report for the first time that MIL-101(Cr) works as a synergistic catalyst for the reduction of imines with trichlorosilane as the hydrogen source. Both ketimines and aldimines were tolerated with this protocol, giving the corresponding amines in moderate to high yields. The operational simplicity as well as mild reaction conditions renders this protocol an attractive approach for the synthesis of amines. Furthermore, a chiral MOF, CMIL-101, was also realized by grafting chiral N-formyl proline derivatives to the open metal sites. Moreover, CMIL-101 exhibited a comparable catalytic performance with its homogeneous counterpart in terms of yields and enantioselectivities.

Synthesis, Reactivity, Functionalization, and ADMET Properties of Silicon-Containing Nitrogen Heterocycles

Silicon-containing compounds have been largely ignored in drug design and development, despite their potential to improve not only the potency but also the physicochemical and ADMET (absorption, distribution, metabolism, excretion, toxicity) properties of drug-like candidates because of the unique characteristics of silicon. This deficiency is in large part attributable to a lack of general methods for synthesizing diverse organosilicon structures. Accordingly, a new building block strategy has been developed that diverges from traditional approaches to incorporation of silicon into drug candidates. Flexible, multi-gram-scale syntheses of silicon-containing tetrahydroquinoline and tetrahydroisoquinoline building blocks are described, along with methods by which diversely functionalized silicon-containing nitrogen heterocycles can be rapidly built using common reactions optimized to accommodate the properties of silicon. Furthermore, to better clarify the liabilities and advantages of silicon incorporation, select compounds and their carbon analogues were challenged in ADMET-focused biological studies.

Unexpected Rearrangement of 2-Bromoaniline under Biphasic Alkylation Conditions

Alkylation of 2-bromoaniline with benzyl bromide under ostensibly basic N-alkylation conditions resulted in migration of bromine from the 2- to the 4-aryl position. Herein we report our studies to elucidate the mechanism of this rearrangement with the objective of suppressing this unexpected outcome. We find that careful choice of reagents is critical, and that this behavior may be extrapolated to alkylation reactions of electron-rich bromo- and iodoanilines in general.