24840-75-3

Usage

Uses

Used in Pharmaceutical Synthesis:
4-(4-CHLORO-PHENYL)-2-METHYL-THIAZOLE is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to impart specific biological activities to the final drug molecules. Its unique structure allows for the development of new therapeutic agents with improved efficacy and selectivity.
Used in Agrochemical Development:
In the agrochemical industry, 4-(4-CHLORO-PHENYL)-2-METHYL-THIAZOLE is used as a building block for the creation of novel agrochemicals. Its incorporation into these compounds can enhance their pesticidal properties, leading to more effective crop protection and increased agricultural productivity.
Used in Antimicrobial Agents:
4-(4-CHLORO-PHENYL)-2-METHYL-THIAZOLE is used as an antimicrobial agent for its demonstrated antibacterial and antifungal properties. It serves as a potential candidate for the development of new antimicrobial agents to combat drug-resistant infections and improve public health.
Used in Research and Development:
In the field of research and development, 4-(4-CHLORO-PHENYL)-2-METHYL-THIAZOLE is utilized to study the structure-activity relationship of thiazole derivatives. This understanding aids in the design and optimization of new compounds with enhanced biological activities and potential applications in various fields, including medicine, agriculture, and materials science.

InChI:InChI=1/C10H8ClNS/c1-7-12-10(6-13-7)8-2-4-9(11)5-3-8/h2-6H,1H3

Upstream product

• 62-55-5 thioacetamide 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 937-20-2 p-chlorophenacyl chloride 
• 25917-49-1 1-(4-chlorophenyl)-2-(p-tolylsulfonyloxy)ethanone 
• 99-91-2 para-chloroacetophenone 
• 3391-10-4 1-(p-chlorophenyl)ethyl alcohol 
• 27993-56-2 1-(4-chlorophenyl)-2-hydroxyethanone 
• 1956-39-4 4-chloroacetophenone oxime 
• 108-24-7 acetic anhydride 

Downstream Products

• 66047-77-6 2-chloro-5-(2-methyl-thiazol-4-yl)-benzenesulfonyl chloride 
• 82672-19-3 4-(p-chlorophenyl)-2-methylthiazole 3-oxide 
• 66047-81-2 2-chloro-5-(2-methyl-thiazol-4-yl)-benzenesulfonamide 
• 1228794-43-1 4-(4'-chlorobiphenyl-4-yl)-2-methyl-1,3-thiazole 
• 24864-19-5 4-([1,1'-biphenyl]-4-yl)-2-methylthiazole 
• 82672-29-5 C₃₂H₂₄Cl₂N₄S₂ 

Relevant academic research and scientific papers

Gold complex containing diphosphine ortho-position carborane ligand as well as preparation method and application of gold complex

The invention relates to a gold complex containing a diphosphine ortho-position carborane ligand as well as a preparation method and an application of the gold complex. The gold complex is prepared bythe following method: dropwise adding an n-BuLi solutio

Access to Thiazole via Copper-Catalyzed [3+1+1]-Type Condensation Reaction under Redox-Neutral Conditions

A new strategy for thiazoles via copper-catalyzed [3+1+1]-type condensation reaction from oximes, anhydrides and potassiumthiocyanate (KSCN) is developed herein. The transformation has good functional group tolerance and various thiazoles were formed smoothly in good to excellent yields under mild reaction conditions. This process involves copper-catalyzed N-O/C-S bond cleavages, activation of vinyl sp2 C-H bond, and C-S/C-N bond formations which are under redox-neutral conditions as well as operational simplicity.

Exploration and Optimization of an Efficient One-pot Sequential Synthesis of Di/tri-substituted Thiazoles from α-Bromoketones, Thioacids Salt, and Ammonium Acetate

Exploration of scope of an optimized one-pot sequential procedure for preparing of 2,4-di- and 2,4,5-tri-substituted thiazoles has been accomplished. The synthesis was performed by the initial formation of a β-keto-thioester intermediate from nucleophilic substitution of α-bromoketones with thioacid potassium salts, followed by treatment with ammonium acetate and one equivalent of acetic acid in toluene to form imine intermediate eventually leading to cyclization yielding thiazoles. This procedure should be highlighted with a flexible way to control the substitution pattern around thiazole ring by choosing appropriately substituted α-bromoketones even containing acid labile functionality and thioacid potassium salts, and thus its applicability is very wide.

A novel and efficient one pot synthesis of 2,4-disubstituted thiazoles and oxazoles using phenyltrimethylammoniumtribromide in ionic liquid

A novel and efficient one-pot procedure has been described for synthesis of 2,4-disubstituted thiazoles and oxazoles from substituted ketones using phenyltrimethylammoniumtribromide as in situ brominating agent followed by reaction with thioamide/thiourea and amides/ureas, respectively in [bmim][BF4] ionicliquid. The advantages of the procedure include avoiding the handling of lacrymetric compounds, hazardous and toxic organic solvents along with good to excellent yield of the products.

Efficient synthesis of 2,4-disubstituted thiazoles under grinding

A simple and convenient protocol is described for the preparation of 2,4-disubstituted thiazoles via a condensation reaction of -halo carbonyl compounds with thiourea or thioacetamide at room temperature, under grinding, in good yields.

A rapid and high-yielding synthesis of thiazoles and aminothiazoles using tetrabutylammonium salts

A convenient method for the synthesis of thiazoles and aminothiazoles by treatment of phenacyl bromides with thioamides/thiourea in the presence of tetrabutylammonium hexafluorophosphate (Bu4NPF6) at room temperature was developed. The products having high yields were formed rapidly (within 15 min). The method is simple, rapid and practical, generating thiazole derivatives in excellent isolated yields. The structures of the newly synthesized products were identified by FT-IR, 1H NMR, 13C NMR spectroscopy and elemental analysis data. The Japan Institute of Heterocyclic Chemistry.

Efficient and expeditious synthesis of di- and trisubstituted thiazoles in PEG under catalyst-free conditions

An efficient and expeditious catalyst-free protocol was developed for the construction of di- and trisubstituted thiazoles from -haloketones and thioureas/thioamides in PEG. The reaction was carried out at ambient temperature, and the products were obtained in excellent isolated yields (91-98%). Additionally, PEG could be recovered easily and was reused without evident loss in activity.

An efficient, catalyst- and solvent-free synthesis of imidazo[1,2-a] pyridines and 2,4-disubstituted thiazoles on grinding

An efficient synthesis of imidazo[1,2-a]pyridines and 2,4-disubstituted thiazoles in excellent yield under catalyst-and solvent-free conditions at room temperature on grinding has been developed. The important features of this method are that it is reasonably fast, very clean, high yielding, simple workup and environmentally benign.

Liquid-phase organic synthesis of thiazoles using poly(ethylene glycol)-bound sulfonyl chloride resin

Reaction of poly(ethylene glycol) (PEG)-bound sulfonic acid with thionyl chloride formed difunctionalized PEG-bound sulfonyl chloride, which was treated with α-hydroxyketones, followed by treatment with thioamides in the presence of potassium carbonate, to afford thiazoles in good yields with a facile workup procedure. Copyright Taylor & Francis Group, LLC.

Efficient synthesis of 2,4-disubstituted thiazoles using ionic liquid?under ambient conditions: a practical approach towards?the?synthesis of Fanetizole

A highly efficient and rapid synthesis of 2-amino-4-arylthiazoles and 2-methyl-4-arylthiazole from α-bromoketone and thiourea/thioamide is described using room temperature ionic liquid at ambient conditions. The method is simple, rapid and practical, generating thiazole derivatives in excellent isolated yields. This protocol is utilized for a commercially feasible synthesis of an anti-inflammatory agent, Fanetizole.