15965-31-8

Usage

Uses

Used in Organic Synthesis:
4-Chloroimidazole is used as a synthetic building block for the development of various chemical compounds. Its application in organic synthesis is attributed to its reactivity and ability to form a wide range of products, making it a valuable component in the creation of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Chloroimidazole is used as an intermediate in the synthesis of various drugs. Its unique chemical structure allows for the development of new therapeutic agents with potential applications in treating a variety of medical conditions.
Used in Agrochemical Industry:
4-Chloroimidazole is also utilized in the agrochemical industry for the synthesis of pesticides and other crop protection agents. Its incorporation into these products helps to enhance their effectiveness in protecting crops from pests and diseases, ultimately contributing to increased agricultural productivity.

InChI:InChI=1/C3H3ClN2/c4-3-1-5-2-6-3/h1-2H,(H,5,6)

Upstream product

• 89108-47-4 4-diazo-4H-imidazole 
• 108-90-7 chlorobenzene 
• 288-32-4 1H-imidazole 
• 129378-52-5 2-tert-butyldimethylsilyl-N,N-dimethylimidazole-1-sulfonamide 

Downstream Products

• 1090511-11-7 C₁₉H₁₉ClN₂O₂ 
• 1090511-10-6 C₁₉H₁₉ClN₂O₂ 
• 1248592-25-7 methyl {2-[(4-chloro-1H-imidazol-1-yl)methyl]phenyl}acetate 
• 1248592-24-6 methyl {2-[(5-chloro-1H-imidazol-1-yl)methyl]phenyl}acetate 
• 872-49-1 N-methyl-5-chloroimidazole 
• 1356009-16-9 tert-butyl 3-(2-(4-chloro-1H-imidazol-1-yl)-5-nitrophenoxy)propylcarbamate 
• 1356009-13-6 tert-butyl 2-(2-(2-(4-chloro-1H-imidazol-1-yl)-5-nitrophenoxy)ethoxy)ethylcarbamate 
• 1356009-06-7 1-(2-(allyloxy)-4-nitrophenyl)-4-chloro-1H-imidazole 
• 1235492-44-0 4-chloro-1-(2-fluoro-6-methoxy-4-nitrophenyl)-1H-imidazole 
• 1235491-92-5 4-chloro-1-(2-methoxy-4-nitrophenyl)-1H-imidazole 
• 1235492-28-0 4-chloro-1-(2,6-difluoro-4-nitrophenyl)-1H-imidazole 
• 1215015-17-0 C₁₅H₁₆Cl₂N₂OS 

Relevant academic research and scientific papers

Synthesis and characterization of new N-(4-(4-chloro-1H-imidazol-1-yl)-3- methoxyphenyl)amide/sulfonamide derivatives as possible antimicrobial and antitubercular agents

In this paper we report the SAR studies of a series of N-(4-(4-chloro-1H- imidazol-1-yl)-3-methoxyphenyl)amide and N-(4-(4-chloro-1H-imidazol-1-yl)-3- methoxyphenyl)sulfonamide derivatives 6(a-o) and 7(a-o), were synthesized in good yields and characterized by 1H NMR, 13C NMR and mass spectral analyses. The preparation of the key intermediate highlights an optimized palladium catalyzed (Pd2(dba)3/RuPhos) Buchwald cross-coupling of intermediate 2 and 3. The newly synthesized compounds were evaluated for their in vitro antibacterial activity against Staphylococcus aureus, (Gram-positive), Escherichia coli and Klebsiella pneumoniae (Gram-negative), antifungal activity against Candida albicans, Aspergillus flavus and Rhizopus sp. and antitubercular activity against Mycobacterium tuberculosis H37Rv, Mycobacterium smegmatis, Mycobacterium fortuitum and MDR-TB strains. The synthesized compounds displayed interesting antimicrobial activity. The compounds 7d, 7f, 7h and 7n displayed significant activity against Mycobacterium tuberculosis H37Rv strain.

Cu-Mn spinel oxide catalyzed regioselective halogenation of phenols and N-heteroarenes

A novel simple, mild chemo- and regioselective method has been developed for the halogenation of phenols using Cu-Mn spinel oxide as a catalyst and N-halosuccinimide as halogenating agent. In the presence of Cu-Mn spinel oxide B, both electron-withdrawing and electron-donating groups bearing phenols gave monohalogenated products in good to excellent yields with highest para-selectivity. The para-substituted phenol gave monohalogenated product with good yield and ortho-selectivity. N-Heteroarenes such as indoles and imidazoles also gave monohalogenated products with high selectivity. Unlike the copper-catalyzed halogenation, the present method works well with electron-withdrawing group bearing phenols and gives comparatively better yields and selectivity. The Cu-Mn spinel catalyst is robust and reused three times under optimized conditions without any loss in catalytic activity. Nonphenolics did not undergo this transformation.

Novel Bicyclic Pyridinones

Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula I as defined herein. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

GLUCAGON RECEPTOR MODULATORS

The present invention provides a compound of Formula (I) or a pharmaceutically acceptable salt thereof wherein R1, R2, R3, A1, A2, A3, A4, L, B1, B2, B3 and B4 are as defined herein. The compounds of Formula I have been found to act as glucagon antagonists or inverse agonists. Consequently, the compounds of Formula I and the pharmaceutical compositions thereof are useful for the treatment of diseases, disorders, or conditions mediated by glucagon.

Novel imidazobenzazepine derivatives as dual H1/5-HT 2A antagonists for the treatment of sleep disorders

A novel imidazobenzazepine template (5a) with potent dual H 1/5-HT2A antagonist activity was identified. Application of a zwitterionic approach to this poorly selective and poorly developable starting point successfully delivered a class of high quality leads, 3-[4-(3-R1-2-R-5H-imidazo[1,2-b][2]benzazepin-11-yl)-1-piperazinyl]- 2,2-dimethylpropanoic acids (e.g., 9, 19, 20, and 21), characterized by potent and balanced H1/5-HT2A receptor antagonist activities and good developability profiles.

IMIDAZOBENZAZEPINE COMPOUNDS FOR THE TREATMENT OF CENTRAL NERVOUS SYSTEM (CNS) DISEASES

This invention relates to novel novel imidazobenzazepine derivatives of formula (I) or a pharmaceutically acceptable salt thereof, for treating diseases and conditions of the central nervous system (CNS), in particular sleep disorders.

NOVEL COMPOUNDS

Compounds of formula (I): are inhibitors of the enzyme Lp-PLA2 and are of use in therapy, in particular for treating atherosclerosis. In Formula (I) R1, R2, R3, R4, R5, R6, X and Y are as d

Syntheses of (trifluoromethyl)imidazoles with additional electronegative substituents, an approach to receptor-activated affinity labels

Electrophilic substitution in 2- and 4-(trifluoromethyl)imidazoles provides derivatives containing one or two nitro, chloro, bromo, or iodo groups. Fluoro and chloro derivatives were also prepared by photochemical trifluoromethylation of the respective haloimidazole. The results demonstrate that (trifluoromethyl)imidazoles behave fairly typically under the conditions of electrophilic nitration and halogenation. Of the alternative routes to the desired bifunctional and trifunctional imidazoles, electrophilic substitution on the preformed (trifluoromethyl)imidazole appears to be the method of choice in most cases. A large number of the products show herbicidal or insecticidal activity.

CARBENIC REACTIONS OF 4-DIAZO-4H-IMIDAZOLE WITH BENZENE DERIVATIVES

The electrophilic behavior of 4H-imidazolylidene is greatly modified by coordinating groups in benzene derivatives undergoing substitution.

HIGH-YIELDING SYNTHESES OF 4(5)-SUBSTITUTED IMIDAZOLES VIA ORGANOLITHIUM INTERMEDIATES. THE UTILITY OF SULPHONAMIDE N-PROTECTION AND SILICON-CONTAINING BLOCKING GROUPS

N-protection of imidazole as its N,N-dimethyl-sulphonamido derivative, and blocking of the 2-position with the triethylsilyl group permits regioselective 5-metallation with sec-butyl-lithium.The resulting organolithium intermediates react with a range of electrophiles and the products are easily deprotected to give the 4(5)-substituted NH-free imidazoles in good to excellent yields.Isolation of the silicon-blocked intermediate is unnecessary and, indeed, is disadvantageous to final yields, making the procedure attractively economical of time.