206535-83-3

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-BROMOPHENYL)-4,5-DIHYDRO-1H-IMIDAZOLE is used as a building block for the synthesis of various pharmaceutical compounds. Its unique structural characteristics and chemical reactivity make it a valuable component in the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
2-(4-BROMOPHENYL)-4,5-DIHYDRO-1H-IMIDAZOLE is used as a building block for the synthesis of various agrochemical compounds. Its structural features and reactivity contribute to the development of new agrochemicals with potential applications in agriculture, such as pesticides and herbicides, to improve crop yield and protect plants from pests and diseases.

Upstream product

• 107-15-3 ethylenediamine 
• 29203-58-5 4-bromo-N-hydroxybenzenecarboximidoyl chloride 
• 1122-91-4 4-bromo-benzaldehyde 
• 623-00-7 4-bromobenzenecarbonitrile 
• 1638253-81-2 3-(4-bromophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-one 

Downstream Products

• 314240-87-4 2-(4-bromophenyl)-1-(tert-butoxycarbonyl)-4,5-dihydro-1H-imidazole 
• 176961-53-8 2-(4-bromophenyl)-1H-imidazole 

Relevant academic research and scientific papers

Visible Light-Promoted Aryl Azoline Formation over Mesoporous Organosilica as Heterogeneous Photocatalyst

N-heterocyclic compounds demonstrate wide applications ranging from natural compound production to coordination chemistry. Usually, the synthesis of N-heterocyclic compounds is conducted under thermal conditions, mostly by Lewis acids or metal-containing compounds as molecular catalysts. Here, we report a photocatalytic route for aryl azoline formation by mesoporous organosilica as visible light-active and heterogeneous photocatalyst. Via formation of aromatic aldehydes with various amines, 2-phenyl-2-imidazoline, 2-phenyl-2-oxazoline, 2-phenyl-2-thiazoline and their derivatives could be formed with high conversion and selectivity. Additionally, the organosilica photocatalyst showed high stability and reusability.

Cu(II) immobilized on Fe3O4@Agarose nanomagnetic catalyst functionalized with ethanolamine phosphate–salicylaldehyde schiff base: A magnetically reusable nanocatalyst for preparation of 2-substituted imidazolines, oxazolines, and thiazolines

Herein we synthesized Cu(II) immobilized on Fe 3 O 4 @Agarose functionalized with ethanolamine phosphate–salicylaldehyde Schiff base (Fe 3 O 4 @Agarose/SAEPH 2 /Cu(II)) as a new and cost-effective nanomagnetic catalyst. The nanomagnetic catalyst was characterized by FT- IR, XRD, VSM, SEM- EDX, TEM, TGA, and ICP techniques and it was found that the particles were about 9–25 nm in size and spherical with entrapment of the Fe 3 O 4 particles in the hollow pore structure of the agarose. The prepared nanomagnetic catalyst showed excellent activity for preparation of 2-substituted imidazolines, oxazolines, and thiazolines. The catalyst is easy to prepare and exhibits higher catalytic activity than some commercially available copper sources. More importantly, this nanomagnetic catalyst can be easily recovered by using a permanent magnet and reused for at least seven cycles without significant deactivation.

PPAR AGONISTS, COMPOUNDS, PHARMACEUTICAL COMPOSITIONS, AND METHODS OF USE THEREOF

Provided herein are compounds and compositions useful in increasing PPARδ activity. The compounds and compositions provided herein are useful for the treatment of PPARδ related diseases (e.g., muscular diseases, vascular disease, demyelinating disease, and metabolic diseases).

Synthesis of benzimidazole and quinoxaline derivatives using reusable sulfonated rice husk ash (RHA-SO3H) as a green and efficient solid acid catalyst

In this work, a simple, rapid and efficient method for the preparation of benzimidazoles and quinoxalines from the condensation of o-phenylene diamines with aldehydes and/or 1,2-dicarbonyl compounds in the presence of sulfonated rice husk ash (RHA-SO3H) as an efficient green catalyst is reported. RHA-SO3H can be easily prepared using a readily available organic compound by simple modification of rice husk ash. All reactions are performed under mild reaction conditions with high to excellent yields. The method is applicable to aromatic, unsaturated and hetero aromatic aldehydes. The advantages of this method are short reaction times, milder conditions, easy work-up, solvent-free conditions and catalyst reusability.

Fe3O4@SiO2@polyionene/Br3- core-shell-shell magnetic nanoparticles: A novel catalyst for the synthesis of imidazole derivatives under solvent-free conditions

New Fe3O4@SiO2@polyionene/Br3- core-shell-shell magnetite nanoparticles were prepared using a co-precipitation method and were used in the syntheses of imidazole derivatives under solvent-free conditions. The polyionene was easily prepared by reacting DABCO and 1,4-dibromo butane in DMF/methanol. It was then added to the previously formed layers and magnetic core-shell nanoparticles (P-MNPs) were functionalized. All the resultant nanoparticles were characterized by transmission electron microscopy (TEM), scanning electron microscopy (SEM), infrared spectroscopy (FTIR), X-ray diffraction (XRD), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), and vibrating sample magnetometry (VSM). The catalyst was readily recovered by simple magnetic decantation and can be recycled several times with no significant loss of catalytic activity.

Ruthenium(II) carbonyl complexes containing pyridoxal thiosemicarbazone and trans-bis(triphenylphosphine/arsine): Synthesis, structure and their recyclable catalysis of nitriles to amides and synthesis of imidazolines

Pyridoxal N(4)-substituted thisemicarbazone hydrochloride ligands (L1-3) were synthesized and reacted with the ruthenium(II) starting complexes [RuHCl(CO)(EPh3)3] (EP or As). The resulting complexes [Ru(CO)(L1-3)(EPh3)2] (1-6) were characterized by elemental analyses and spectroscopic techniques. The molecular structure of complex 5 was identified by means of single crystal X-ray diffraction analysis. The catalytic activity of the new complexes was evaluated for the selective hydration of nitriles to primary amides and also the condensation of nitriles with ethylenediamine under solvent free conditions. The processes were operative with aromatic, heteroaromatic and aliphatic nitriles, and tolerated several substitutional groups. The studies on the effect of substitution over thiosemicarbazone, reaction time, temperature, solvent and catalyst loading were carried out in order to find the best catalyst in this series of complexes and favourable reaction conditions. A probable mechanism for both the catalytic reactions of nitrile has also been proposed. The catalyst was recovered and recycled in the hydration of nitriles for five times without any significant loss of its activity.

Peculiarities of the cascade cleavage of the polarized C - C-fragment in α-ketoacetylenes on reaction with ethylene diamine

The reaction of diarylketoacetylenes with ethylenediamine (EDA) leads to arylmethylketones and 2-substituted imidazoline derivatives. This transformation involves complete cleavage of the triple bond via initial intermolecular Michael-addition with subsequent intramolecular Michaeladdition. Final fragmentation can be presented as a retro-Mannich reaction, accompanied by three formal reductive stages (formation of three C-H bonds), while the other carbon undergoes a formal oxidation, in which three C-N bonds (C-N and C=N) are formed. ARKAT-USA, Inc.

Synthesis of 2-aryl/heteroaryloxazolines from nitriles under metaland catalyst-free conditions and evaluation of their antioxidant activities

The synthesis of structurally diverse 2-aryl/heteroaryloxazolines from nitriles and aminoalcohols has been achieved under metal- and catalyst-free conditions in good to excellent yields. An array of functional groups are well-tolerated, thus, allowing the introduction of many important biologically active motifs such as azoles, ring-fused azoles, saturated heterocyclics, and amines in 2-aryloxazoline scaffolds. An evaluation of the antioxidant properties using the DPPH (diphenyl picryl hydrazyl) assay method shows the pyrrole-functionalized 2-aryloxazoline to be the best antioxidant among all the synthesized 2-aryl/heteroaryloxazolines.

Semi-empirical computation on mechanism of imidazolines and benzimidazoles synthesis and their QSAR studies

A green, mild and anaerobic synthesis of imidazolines and benzimidazoles from aldehydes and diamines using I2/KI/K2CO3/H2O system has been investigated by semi-empirical methods. The observed efficient direction of the above synthesis has been modeled from a comparison of the energies of four possible transition states arising from mono and di additions of iodines in the configured molecules. In the reaction I1 B is the most favorable transition state [TS] which is shown to be 20 Kcal/mol by PM3 analyses. The resulting trends of relative transition states energies are in excellent agreement with the experimental observations. Also, the bond order, bond length, heat of formation is in good agreement to the formation of product B. In order to establish the suitable mechanism of the reaction a quantitative structure activity relationship analysis has been made using hydrophobicity as the molecular descriptor. In this analysis the values of refractivity, polarizability, hydration energy, electron affinity, ionization potential and dipole moment of the compounds have been correlated with their hydrophobicity which has been taken as the molecular property.

Trichloroisocyanuric acid as an efficient homogeneous catalyst for the chemoselective synthesis of 2-substituted oxazolines, imidazolines and thiazolines under solvent-free condition

Trichloroisocyanuric acid, as a commercially available and inexpensive catalyst, was used in a new, facile and efficient procedure for the synthesis of 2-oxazolines, 2-imidazolines and 2-thiazolines through the reaction of nitriles with 2-aminoethanol, ethylenediamine or 2-aminoethanethiol under solvent-free conditions.