33468-69-8

Usage

Uses

Used in Pharmaceutical Industry:
4-(Trifluoromethyl)-1H-imidazole is used as an inhibitor of sweet almond β-glucosidase, a key enzyme involved in the breakdown of complex carbohydrates. This application is significant in the development of treatments for various metabolic disorders and conditions related to carbohydrate metabolism.
Used in Chemical Synthesis:
4-(Trifluoromethyl)-1H-imidazole serves as a reagent in the synthesis of 3-substituted 2-aminopyridines. This is achieved through the displacement of 3-fluoro-2-nitropyridine, a reaction that highlights the compound's versatility in organic chemistry and its potential use in creating a range of pharmaceutically relevant molecules.

InChI:InChI=1/C4H3F3N2/c5-4(6,7)3-1-8-2-9-3/h1-2H,(H,8,9)

Upstream product

• 60-35-5 acetamide 
• 431-35-6 3-bromo-1,1,1-trifluoroacetone 
• 75-63-8 Bromotrifluoromethane 
• 135284-99-0 imidazole tetramethylammonium salt 
• 100-97-0 hexamethylenetetramine 
• 431-67-4 1,1-dibromo-3,3,3-trifluoroacetone 
• 50-00-0 formaldehyd 
• 111269-38-6 1,1,1-trifluoro-3-(dimethylhydrazono)-2-propanone 
• 77287-34-4 formamide 
• 288-32-4 1H-imidazole 
• 1184-76-5 difluorodiiodomethane 
• 91944-47-7 3,3,3-Trifluoropyruvaldehyde 
• 2314-97-8 iodotrifluoromethane 

Downstream Products

• 57090-88-7 1H-imidazole-4-carbonitrile 
• 1215198-23-4 (S)-methyl 3-cyclohexyl-2-(4-(trifluoromethyl)-1H-imidazol-1-yl)propanoate 
• 1236363-57-7 1-(4-bromobenzyl)-4-trifluoromethyl-1H-imidazole 
• 1393125-28-4 1-(2-methyl-4-nitrophenyl)-4-(trifluoromethyl)-1H-imidazole 
• 1319157-20-4 4-(3,4-dichlorophenyl)-6-[4-(trifluoromethyl)imidazol-1-yl]pyrimidine 
• 1613395-20-2 1-[1-(4-fluorophenyl)-5-isopropylpyrazol-4-yl]-3-[4-(trifluoromethyl)-imidazol-1-yl]pyrrolidin-2-one trifluoroacetate 
• 1170734-96-9 C₁₂H₉F₃N₂O₂ 
• 1393126-55-0 (+/-)-methyl 4-(3-methyl-1-(4-(4-(trifluoromethyl)-1H-imidazol-1-yl)phenyl)butoxy)benzoate 
• 1393125-91-1 1-(2,6-dimethyl-4-nitrophenyl)-4-(trifluoromethyl)-1H-imidazole 
• 1323404-02-9 3-{1-OXO-4-[4-(4-TRIFLUOROMETHYL-IMIDAZOL-1-YL METHYL)-BENZYLOXY]-1,3-DIHYDRO-ISOINDOL-2-YL}-PIPERIDINE-2,6-DIONE 
• 1215015-20-5 C₁₆H₁₆ClF₃N₂OS 

Relevant academic research and scientific papers

Perfluoroalkylation of imidazoles by electrochemically induced srn1 substitution

Indirect electrochemical reduction, by means of aromatic anion radical mediators, of perfluoroalkyl halides in the presence of imidazolate or of substituted imidazolate anions yields the corresponding perfluoroalkylated imidazoles along an SRN1 mechanism.

HETEROCYCLIC MODULATORS OF LIPID SYNTHESIS AND COMBINATIONS THEREOF

Heterocyclic modulators of lipid synthesis are provided as well as pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising such compounds; and methods of treating conditions characterized by disregulation of a fatty acid synthase pathway by the administration of such compounds and combinations of such compounds and other therapeutic agents.

FLUOROISOQUINOLINE SUBSTITUTED THIAZOLE COMPOUNDS AND METHODS OF USE

The invention relates to thiazole compounds of Formula (I) and compositions thereof useful for treating diseases mediated by protein kinase B (PKB) where the variables have the definitions provided herein. The invention also relates to the therapeutic use of such thiazole compounds and compositions thereof in treating disease states associated with abnormal cell growth, cancer, inflammation, and metabolic disorders.

ORGANIC COMPOUNDS

The present invention provides a compound of formula I: said compound is inhibitor of aldosterone synthase (CYP11B2), and/or 11beta-hydroxylase (CYP11B1), and/or aromatase, and thus can be employed for the treatment of a disorder or disease mediated by al

3-dimethylhydrazono-1,1,1-trifluoro-2-propanone as a useful synthetic equivalent of trifluoropyruvaldehydeapplication to synthesis of fluorine-containing heterocycles

3-Dimethylhydrazono-1,1,1-trifluoro-2-propanone (4) which is easily obtainable from formaldehyde dimethylhydrazone and trifluoroacetic anhydride was found to be an usuful synthetic equivalent of trifluoropyruvaldehyde for the synthesis of fluorine-containing heterocycles. With the use of 4, 4-trifluoromethylimidazoles and 2-trifluoromethylquinoxaline were successfully synthesized.

A convenient synthesis of perfluoroalkylated and fluorinated-aryl nitrogen bases by electrochemically induced SRN1 substitution

Indirect electrochemical reduction, by means of an aromatic anion mediator, of perfluoroalkyl halides (CF3Br, n-C4F9I, n-C6F13I, I(CF2)4I) in the presence of imidazole, 4(5)-nitroimidazole, 2-methyl-5-nitroimidazole, 2-(4′-methoxyphenyl)imidazole, imidazole-2-carboxaldehyde, 4(5)-nitroimidazole-2-carboxaldehyde, 5(6)-nitrobenzimidazole, purines (adenine, hypoxanthine, xanthine, theophylline, lumazine) and pyrimidine anions (uracil, cytosine, barbituric acid) yields the corresponding C-perfluoroalkylated nitrogen bases by an SRN1 mechanism. Aromatic nucleophilic substitution of some fluorinated aryl halides 1-iodo-2-(trifluoromethyl)benzene and 1-(4′-iodo-tetrafluorophenyl)-imidazole was also investigated and it was found that 1-iodo-2-(trifluoromethyl)benzene could react successfully under redox-catalyzed conditions with imidazole, 2-(4′-methoxyphenyl)imidazole anion, and uracil anion to give the corresponding 5-(fluorinated-aryl) nitrogen bases. In the case of 1-(4′-iodo-tetrafluorophenyl)imidazole, direct electrochemical radical nucleophilic substitution with 2-methyl-5-nitroimidazole and uracil was possible in DMSO. In this way new, 4-[2′,3′,5′,6′-tetrafluoro-4′-(imidazol-1″- yl)phenyl] nitrogen bases were obtained in good yields.

Photoinduced Electron-transfer Reaction of Difluorodiiodomethane with Azaaromatic Compounds and Enamines

Irradiation of difluorodiiodomethane 1 with pyrroles, indole and imidazoles in dimethylformamide gives the corresponding trifluoromethylated products, whereas irradiation with enamines results in 2-trifluoromethyl ketones.A photoinduced electron-transfer mechanism is proposed.

Electrochemically Induced Nucleophilic Substitution of Perfluoroalkyl Halides. An Example of a Dissociative Electron-Transfer-Induced Chemical Reaction

Nucleophilic substitution of perfluoroalkyl halides can be induced electrochemically.The reaction mechanism is a slightly modified version of the classical SRN1 mechanism in which the reaction is triggered by dissociative electron transfer, not

Syntheses of Trifluoromethyl Heterocycles

Mono and bicyclic heterocycles bearing trifluoromethyl substituent have been synthesized and characterized by spectral studies. 4(5)-Trifluoromethylimidazole (3) is prepared from the reaction of 3,3-dibromo-1,1,1-trifluoroacetone (2) with formaldehyde and ammonia.N-Methylation of 3 by phase transfer reaction gives 1-methyl-4-trifluoromethylimidazole (4). 2-Amino-4-trifluoromethylimidazole (5) is similarly obtained from 3-bromo-1,1,1-trifluoroacetone (1) and thiourea.The reaction of 1 with 2-aminopyridine and 2-aminothiazole gives 2-trifluoromethylimidazopyridine (7) and 6-trifluoromethylimidazothiazole (9) respectively.

Photochemical Perfluoroalkylation of Imidazoles

Imidazole and its derivatives undergo facile trifluoromethylation or perfluoroalkylation, in methanol solution at ambient temperature, following radical dissociation of RFI by γ or UV irradiation.In the case of imidazole, attack occurs preferen