27423-81-0

Usage

Uses

Used in Pharmaceutical Industry:
2-(3-CHLORO-PHENYL)-1H-IMIDAZOLE is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to be incorporated into complex molecular structures, enhancing the development of new drugs with improved therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 2-(3-CHLORO-PHENYL)-1H-IMIDAZOLE is utilized as a building block for the creation of agrochemicals, such as pesticides and fungicides, due to its potential antifungal and antibacterial properties, which can help protect crops and enhance agricultural productivity.
Used in Research and Development:
2-(3-CHLORO-PHENYL)-1H-IMIDAZOLE is employed in research and development for the creation of new drugs and chemical compounds. Its versatile reactivity and functional group compatibility make it a valuable component in the design and synthesis of innovative molecules with potential applications in medicine and other industries.

InChI:InChI=1/C9H7ClN2/c10-8-3-1-2-7(6-8)9-11-4-5-12-9/h1-6H,(H,11,12)

Upstream product

• 108-90-7 chlorobenzene 
• 50846-98-5 2-Diazo-2H-imidazole 
• 27429-86-3 2-(3-chlorophenyl)-4,5-dihydro-1H-imidazole 
• 288-32-4 1H-imidazole 
• 108-42-9 3-chloro-aniline 
• 618-46-2 m-Chlorobenzoyl chloride 
• 107-15-3 ethylenediamine 
• 766-84-7 3-chloro-benzonitrile 

Downstream Products

• 1160826-47-0 C₁₆H₁₀ClN₃O₃ 

Relevant academic research and scientific papers

Synthesis, antimicrobial activities and binding mode analysis of some novel N-substituted imidazoles and nitroimidazoles

Novel N-((2-(aryl)-imidazol-1-yl) methyl)-anilines 2a-n and 1-(3'-arylamino-2'- hydroxypropyl)-2-methyl-4-nitroimidazoles 4a-g have been synthesized. The compounds have been characterized on the basis of elemental analysis and spectral data. All the compounds were evaluated for their antibacterial activities. Among the synthesized compounds, compounds 2m, 2n and compounds 4c, 4e exhibited highest inhibitory activity against all the bacterial strains, comparable to the standard drug ciprofloxacin. Binding mode analysis of the highest active compounds was carried out in the active site of GlcN-6-P synthase (2VF5).

Multi-wall carbon nanotube supported manganese(III) porphyrin: An efficient and reusable catalyst for oxidation of 2-imidazolines with sodium periodate

The oxidation of 2-substituted imidazolines with sodium periodate catalyzed by tetrakis(p-aminophenyl)-porphyrinatomanganese(III) chloride, [Mn(TNH 2PP)Cl], supported on functionalized multi-wall carbon nanotubes is reported. A wide variety of 2-imidazolines were efficiently converted to their corresponding imidazoles by this catalytic system. When the same reaction was subjected to ultrasonic irradiation, the reaction times were reduced significantly and the product yields were increased. This catalyst could be reused several times without significant loss of activity. The effects of reaction parameters such catalyst amount, choice of solvent, and the effects of ultrasonic irradiation on the catalytic activity have been investigated.

Rapid and efficient biomimetic oxidation of 2-imidazolines to their corresponding imidazoles with NaIO4 catalyzed by Mn(salophen)Cl

Rapid and efficient oxidation of 2-substituted imidazolines with sodium periodate is reported. The Mn(III)-salophen/NaIO4 catalytic system efficiently converted 2-imidazolines to their corresponding imidazoles at room temperature in 2: 1, CH3CN/H2O mixture.

Dehydrogenation of 2-imidazolines with sodium periodate catalyzed by manganese(III) tetraphenylporphyrin

In the present work, dehydrogenation of 2-substituted imidazolines with sodium periodate in the presence of tetraphenylporphyrinatomanganese(III) chloride, [Mn(TPP)Cl], is reported. A wide variety of 2-imidazolines efficiently converted to their corresponding imidazoles by [Mn(TPP)Cl]/NaIO4 catalytic system at room temperature in 1:2, CH3CN/H2O mixture. The effect of reaction parameters such as kind of solvent and catalyst amount was also investigated.

Oxidation of 2-imidazolines to 2-imidazoles with sodium periodate catalyzed by polystyrene-bound manganese(III) porphyrin

In the present work, the dehydrogenation of 2-substituted imidazolines with sodium periodate in the presence of tetraphenylporphyrinatomanganese(III) chloride supported on polystyrene-bound imidazole, [Mn(TPP)Cl@PSI] is reported. A wide variety of 2-imidazolines were efficiently converted to their corresponding imidazoles by the [Mn(TPP)Cl@PSI]/NaIO4 catalytic system in a 1:2 CH3CN/H2O mixture under agitation with magnetic stirring. Ultrasonic irradiation enhanced the catalytic activity of this catalyst in the oxidation of 2-imidazolines and this led to shorter reaction times and higher product yields. This catalyst could be reused several times without significant loss of its catalytic activity.

Synthesis, antimicrobial and antimycobacterial evaluation of [2-(substituted phenyl)-imidazol-1-yl]-pyridin-3-yl-methanones

A series of [2-(substituted phenyl)-imidazol-1-yl]-pyridin-3-yl-methanones (111) were synthesized and screened for their antimicrobial and antimycobacterial activities. Further, a series of [2-(substituted phenyl)-benzimidazol-1-yl]-pyridin-3-yl-methanones (1220) reported in our earlier study was also screened for their antimycobacterial activity. The antimycobacterial activity results indicated that [2-(4-Nitro-phenyl)-imidazol- 1-yl]-pyridin-3-yl-methanone (8, minimum inhibitory concentration [MIC]=3.13 g) was equipotent as standard drug ciprofloxacin and [2-(4-Nitro-phenyl)- benzimidazol-1-yl]-pyridin-3-yl-methanone (16, MIC=1.56 g) was equipotent as standard drug ethambutol. The results of antimicrobial screening demonstrated that 2-[1-(Pyridine-3-carbonyl)-1H-imidazol-2-yl]-benzoic acid (compound 11, MIC=0.002 g) was two times more effective than standard drug ciprofloxacin (MIC=0.004 g) against tested bacterial strains and [2-(2,5-Dimethyl-phenyl)- imidazol-1-yl]-pyridin-3-yl-methanone (compound 3, MIC=0.005 g) was equipotent to the reference compound, fluconazole against tested fungal strains.

Synthesis, antimicrobial and antiviral evaluation of substituted imidazole derivatives

In the present study, we have synthesized 2-(substituted phenyl)-1H-imidazole (1-12) and (substituted phenyl)-[2-(substituted phenyl)-imidazol-1-yl]-methanone (13-26) analogues and screened them for their antimicrobial activity against Gram positive, Gram negative and fungal species. The results of antibacterial study indicated that compounds 15, 17 and 24 showed appreciable antibacterial activity and compound 26 emerged as the most potential antifungal agent. The results of SAR studies indicated that the presence of electron withdrawing groups is necessary for the antimicrobial activity of the synthesized compounds. The results of the present study indicated that compounds 15, 17 and 24 might be of interest for the identification of new antimicrobial molecules as their antibacterial activity is equivalent to the standard drug norfloxacin. Further, the antiviral screening of (substituted phenyl)-[2-(substituted phenyl)-imidazol-1-yl]-methanones (13-26) against a panel of viral strains indicated that compounds 16 and 19 can be selected as lead compounds for the development of novel antiviral agents.

Direct Oxidative Conversion of Benzoyl Chlorides to 2-Imidazoles Using Heteropolyacids

The reaction of benzoyl chlorides with ethylenediamine in the presence of catalytic amounts of Keggin-type heteropolyacids led to oxidative conversion of benzoyl chlorides to the corresponding 2-imidazoles in good yields.

An efficient synthesis of 2-arylimidazoles by oxidation of 2-arylimidazolines using activated carbon-O2 system and its application to palladium-catalyzed Mizoroki-Heck reaction

Oxidative conversion of 2-substituted imidazoline (dihydroimidazole) to the corresponding imidazole was achieved by an activated carbon-O2 system. Also, the 2-arylimidazolines and 2-arylimidazoles have been found to work as simple ligands in the palladium-catalyzed Mizoroki-Heck reaction.

Mild, efficient, and chemoselective dehydrogenation of 2-imidazolines, bis-imidazolines, and N-substituted-2-imidazolines with potassium permanganate supported on montmorillonite K-10

Different types of 2-imidazolines, bis-imidazolines, and N-substituted-2-imidazolines are efficiently oxidized to their corresponding imidazoles with potassium permanganate (KMnO4) supported on montmorillonite K-10 under very mild conditions. The procedure is very simple and no strict conditions were required. Selective dehydrogenation of 2-alkyl-2-imidazolines in the presence of 2-aryl-2-imidazolines is a noteworthy advantage of this method and can be considered as a useful practical achievement in these reactions.