780-20-1

Usage

Uses

Used in Pharmaceutical Industry:
4-Bromo-N-benzylideneaniline is used as an intermediate in the synthesis of pharmaceuticals for its ability to form stable complexes with various metal ions, which can enhance the properties and effectiveness of certain drugs.
Used in Agrochemical Industry:
4-Bromo-N-benzylideneaniline is used as an intermediate in the production of agrochemicals, contributing to the development of more effective and stable pesticides and other agricultural chemicals.
Used in Coordination Chemistry:
4-Bromo-N-benzylideneaniline is used as a ligand in coordination chemistry for its ability to form stable complexes with various metal ions, which can be useful in the development of new materials and catalysts.
Used in Dye and Pigment Manufacturing:
4-Bromo-N-benzylideneaniline is used in the manufacturing of dyes and pigments due to its color-producing properties, contributing to the creation of a wide range of colors for various applications.

InChI:InChI=1/C13H10BrN/c14-12-6-8-13(9-7-12)15-10-11-4-2-1-3-5-11/h1-10H/b15-10+

Upstream product

• 110-86-1 pyridine 
• 64-17-5 ethanol 
• 15829-45-5 (E)-benzyliden-aniline; compound with bromine (1:2) 
• 60-29-7 diethyl ether 
• 100-52-7 benzaldehyde 
• 106-40-1 4-bromo-aniline 
• 110788-31-3 N-(p-bromophenyl)triphenylarsine imide 
• 26456-05-3 10-methylacridinium perchlorate 
• 586-78-7 para-nitrophenyl bromide 
• 100-51-6 benzyl alcohol 
• 100-42-5 styrene 
• 1967-25-5 4-bromophenylurea 
• 94-41-7 benzalacetophenone 
• 100-46-9 benzylamine 

Downstream Products

• 149742-50-7 4-bromo-N-(4-nitrobenzylidene)aniline 
• 538-51-2 benzylidene phenylamine 
• 3489-08-5 (m-nitrobenzylidene)-p-bromoaniline 
• 861556-73-2 4-[1-(4-bromo-phenyl)-3,4-diphenyl-[1,3]diazetidin-2-yl]-phenol 
• 2879-83-6 N-benzyl-N-(4-bromophenyl)amine 
• 1689-73-2 N-(p-hydroxybenzylidene)aniline 
• 2028-85-5 (4-bromophenyl)diazonium chloride 
• 23990-54-7 3-(4-bromo-phenyl)-1,1-dioxo-2-phenyl-1λ⁶-thiazolidin-4-one 
• 6017-81-8 N-Benzyliden-N-pikryl-4-brom-anilinium-chlorid 
• 10480-35-0 1-(4-bromophenyl)-4,5-dihydro-5-phenyl-1H-1,2,3-triazole 
• 76086-97-0 3-[(4-Bromo-phenylamino)-phenyl-methyl]-1,3-dihydro-indol-2-one 
• 33912-40-2 1-(4-bromophenyl)-4-phenylazetidin-2-one 
• 76086-79-8 4-[(4-Bromo-phenylamino)-phenyl-methyl]-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one 
• 37871-90-2 (3R,4S)-1-(4-Bromo-phenyl)-3,4-diphenyl-azetidin-2-one 

Relevant academic research and scientific papers

Cobalt-Catalyzed Deoxygenative Hydroboration of Nitro Compounds and Applications to One-Pot Synthesis of Aldimines and Amides

The commercially available and bench-stable Co(acac)2 ligated with bis[(2-diphenylphosphino)phenyl] ether (dpephos) was employed for selective room temperature hydroboration of nitro compounds with HBPin (TOF up to 4615 h?1), tolerating halide, hydroxy, amino, ether, ester, lactone, amide and heteroaromatic functionalities. These reactions offered a direct access to a variety of N-borylamines RN(H)BPin, which were in situ treated with aldehydes and carboxylic acids to produce a series of aldimines and secondary carboxamides without the need for dehydrating and/or coupling reagents. Combination of these transformations in a sequential one-pot manner allowed for direct and selective synthesis of aldimines and secondary carboxamides from readily available and inexpensive nitro compounds.

Redox-Neutral Imination of Alcohol with Azide: A Sustainable Alternative to the Staudinger/Aza-Wittig Reaction

The traditional Staudinger/aza-Wittig reaction represents one of the most powerful tools for imine formation. However, for this multistep procedure, the sacrificial phosphine has to be used, resulting in difficulties in the purification process and waste disposal at the same time. Here, we report a redox-neutral azide-alcohol imination methodology enabled by a base-metal nickel PN3 pincer catalyst. The one-step, waste-free, and high atom-economical features highlight its advantages further. Moreover, mechanistic insight suggests a non-metal-ligand cooperation pathway based on the observation of an intermediate and density functional theory calculations.

Direct synthesis of imines from nitro compounds and biomass-derived carbonyl compounds over nitrogen-doped carbon material supported Ni nanoparticles

The selective synthesis of imines from biomass-derived chemicals over heterogeneous non-noble metal catalysts is of great importance for organic transformation. Herein, non-noble heterogeneous nitrogen-doped carbon supported Ni catalysts (abbreviated as Ni/CN-MgO-T, whereTrepresents the pyrolysis temperature) have been facilely prepared from the simple pyrolysis of Ni precursors and biomass, and Ni/CN-MgO-600 with the smallest size of Ni nanoparticles demonstrated the highest catalytic activity. The reductive coupling of nitroarenes and carbonyl compounds could be performed under mild conditions (80 °C, and 10 bar H2), affording structurally-diverse imines with high to excellent yields (84.2-98.1%). Thanks to the mild reaction conditions, the developed method showed good tolerance to other functional groups such as nitriles, halogen and vinyl groups.

Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles

A straightforward and selective reduction of nitroarenes with various alcohols was efficiently developed using an iron catalyst via a hydrogen transfer methodology. This protocol led specifically to imines in 30-91% yields, with a good functional group tolerance. Noticeably, starting from o-nitroaniline derivatives, in the presence of alcohols, benzimidazoles can be obtained in 64-72% yields when the reaction was performed with an additional oxidant, DDQ, and quinoxalines were prepared from 1,2-diols in 28-96% yields. This methodology, unprecedented at iron for imines, also provides a sustainable alternative for the preparation of quinoxalines and benzimidazoles.

Metal-free regioselective C-H amination for the synthesis of pyrazole-containing 2H-indazoles

A general and practical regioselective approach for the C-H amination of 2H-indazoles under transition-metal-free conditions was developed. A series of substrates were tested showing eminent functional group tolerance and affording the C-N functionalization products in good to excellent yields. Mechanism studies revealed that a radical process was involved in this transformation.

Rhodium catalyzed multicomponent dehydrogenative annulation: one-step construction of isoindole derivatives

A strategy for one-pot synthesis of isoindoles is describedviaa catalytic multicomponent dehydrogenative annulation of diarylimines, vinyl ketones and simple amines. In the presence of a rhodium catalyst and Cu oxidant, four C-H and two N-H bonds are activated along with the formation of one new C-C and two new C-N bonds, leading to a series of isoindole derivatives in good to very high isolated yields.

A highly stereoselective oxidation and an easy one pot elimination methodology for 3-allyl-3-phenylthio-β-lactams

A novel, facile, highly efficient and stereoselective protocol for the synthesis of cis-3-allyl-3-phenylsulfinyl-β-lactams and 3-allylidene-β-lactams from cis-3-allyl-3-phenylthio-β-lactams using Selectfluor both as an oxidizing agent and as an eliminating agent with temperature as a control parameter over the reaction outcome has been reported. The methodology is able to conquer the earlier reported shortcomings of long reaction time (24–90 hrs.) and lack of control over product ratio. The synthesized compounds will serve as important synthons for compounds of enhanced biological activity and potency.

Amino-functionalized zirconium and cerium MOFs: Catalysts for visible light induced aerobic oxidation of benzylic alcohols and microwaves assisted N-Alkylation of amines

Herein we report that mixed zirconium-cerium-MOFs with amino-functionalized linkers (2-amino-1,4-benzenedicarboxylate, BDC-NH2, and 4-aminonaphthalene-2,6-dicarboxylate, NDC-NH2) act as effective non-noble-metal-based heterogeneous c

Ionic-Liquid-Catalyzed Synthesis of Imines, Benzimidazoles, Benzothiazoles, Quinoxalines and Quinolines through C?N, C?S, and C?C Bond Formation

We report the tetramethyl ammonium hydroxide catalyzed oxidative coupling of amines and alcohols for the synthesis of imines under metal-free conditions by utilizing oxygen from air as the terminal oxidant. Under the same conditions, with ortho-phenylene diamines and 2-aminobenzenethiols the corresponding benzimidazoles and benzothiazoles were obtained. Quinoxalines were obtained from ortho-phenylene diamines and 1-phenylethane-1,2-diol, the conditions were then extended to the synthesis of quinoline building blocks by reaction of 2-amino benzyl alcohols either with 1-phenylethan-1-ol or acetophenone derivatives. The formation of C?N, C?S and C?C bonds was achieved under metal-free conditions. A broad range of amines (aromatic, aliphatic, cyclic and heteroaromatic) as well as benzylic alcohols including heteroaryl alcohols reacted smoothly and provided the desired products. The mild reaction conditions, commercially available catalyst, metal-free, good functional-group tolerance, broad range of products (imines, benzimidazoles, benzothiazoles, quinoxalines and quinolines) and applicability at gram scale reactions are the advantages of the present strategy.

Functional POM-catalyst for selective oxidative dehydrogenative couplings under aerobic conditions

Development of selective and efficient reusable catalytic systems for sustainable chemical production under benign conditions is attractive and received much attention. Herein, we report a rod-shaped octadecyl trimethylammonium functionalized Keggin-type polyoxometalate [PMO12O40] hybrids (OTA-POM) as an efficient heterogeneous catalyst for selective oxidative dehydrogenative couplings under aerobic conditions without any additive or external base. The catalyst recovery and subsequent five successive recyclability studies of hybrid POM confirms the heterogeneous nature of present catalytic system.