2227-72-7

Basic information

• Product Name: Thiazole, 2-(4-chlorophenyl)-4-phenyl-
• CAS NO: 2227-72-7
• Molecular Formula: C15H10ClNS
• Molecular Weight: 271.77
• Mol File: 2227-72-7.mol

Chemical Properties

• CAS DataBase Reference: Thiazole, 2-(4-chlorophenyl)-4-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Thiazole, 2-(4-chlorophenyl)-4-phenyl-(2227-72-7)
• EPA Substance Registry System: Thiazole, 2-(4-chlorophenyl)-4-phenyl-(2227-72-7)

Safety Data

• Hazardous Substances Data: 2227-72-7(Hazardous Substances Data)

Upstream product

• 100008-77-3 4-Chloro-dithiobenzoic acid 2-oxo-2-phenyl-ethyl ester 
• 7257-94-5 1-phenyl-2-(p-tolylsulfonyloxy)ethanone 
• 2521-24-6 4-chlorothiobenzamide 
• 21011-44-9 4-(4-chloro-thiobenzoyl)-morpholine 
• 4098-17-3 1-(1-azido-2-iodoethyl)benzene 
• 1679-18-1 4-Chlorophenylboronic acid 
• 5399-30-4 2-oxo-2-phenylethylthiocyanate 
• 104-86-9 4-chlorobenzylamine 
• 98-86-2 acetophenone 
• 536-74-3 phenylacetylene 
• 100-41-4 ethylbenzene 
• 27149-26-4 2-(4-chlorophenyl)thiazole 
• 98-80-6 phenylboronic acid 
• 637-87-6 1-Chloro-4-iodobenzene 

Relevant articles and documents

Ynamide-Mediated Thioamide and Primary Thioamide Syntheses

Environmentally friendly ynamide-mediated thioamidation of monothiocarboxylic acids with amines or ammonium hydroxide for the syntheses of thioamides and primary thioamides is described. Simple and mild reaction conditions enable the reaction to tolerate a wide variety of functional groups such as hydroxyl group, ester, tertiary amine, ketone, and amide moieties. Readily available NaSH served as the sulfur source, avoiding the use of toxic, expensive, and malodorous organic sulfur reagents and making this strategy environmentally friendly and practical. Importantly, the stereochemical integrity of α-chiral monothiocarboxylic acids was maintained during the activation step and subsequent aminolysis process, thus offering a racemization-free strategy for peptide C-terminal modification. Furthermore, a number of thioamide-modified drugs were prepared in good yields by using this protocol and the synthesized primary thioamides were transformed into backbone thiazolyl modified peptides.

Cascade reactions to 2,4-disubstituted thiazoles via ligand-free palladium(II)-catalyzed C(sp)–C(sp2) coupling

A simple construction for various 2,4-disubstituted thiazoles via palladium(II)-catalyzed C(sp)–C(sp2) and C-N cascade coupling reactions was developed. Various substrates can be tolerated with good yields. And its ligand-free condition demonst

Br?nsted acid-promoted thiazole synthesis under metal-free conditions using sulfur powder as the sulfur source

A Br?nsted acid-promoted sulfuration/annulation reaction for the one-pot synthesis of bis-substituted thiazoles from benzylamines, acetophenones, and sulfur powder has been developed. One C-N bond and multi C-S bonds were selectively formed in one pot. The choice of the Br?nsted acid was the key to the high efficiency of this transformation under metal-free conditions.

Preparation method of 2, 4-disubstituted thiazole compound

The invention discloses a preparation method of a 2, 4-disubstituted thiazole compound. The method comprises the following steps: carrying out heating reflux reaction on substituted carboxylic acid inthionyl chloride to obtain yellow transparent liquid, and adding dichloromethane to dilute for later use; in an ice bath, slowly dropwise adding the substituted acyl chloride solution into ammonia water while stirring, stirring at room temperature to separate out a white solid, and after the reaction is finished, carrying out suction filtration, washing and drying to obtain substituted amide; carrying out reflux on substituted amide and Lawesson in tetrahydrofuran, carrying out rotary evaporation to remove the solvent after the reaction is finished, and carrying out column purification on thecrude product to obtain substituted sulfamide. The preparation method comprises the following steps: putting substituted sulfamide, ethanol, triethylamine and an alpha-bromocarbonyl compound into a pressure reaction tank, putting the pressure reaction tank into an annular focusing single-mode microwave synthesizer for irradiation, and cooling with compressed air to obtain a target compound. Basedon microwave synthesis, the invention has the advantages of short reaction time, high yield, high heating speed, environment friendliness and the like, and provides a microwave synthesis method of a2, 4-disubstituted thiazole compound.

Visible Light-Induced Difunctionalization of Alkynes: The Synthesis of Thiazoles and 1,1-Dibromo-1-en-3-ynes

A visible light-induced cascade cyclization of thioamides with alkynes was developed to synthesize 1,3-thiozoles. The sulfur radical generated from thioamide via the single-electron transfer (SET) pathway was promoted by photocatalysis as a key intermediate in this reaction. When bromoalkynes were used as the substrate, the self-coupling products 1,1-dibromo-1-en-3-ynes were obtained in moderate yields, and an energy transfer pathway for this transformation promoted by visible-light photocatalysis was proposed.

Aryliodoazide synthons: A different approach for diversified synthesis of 2-aminothiazole, 1,3-thiazole, and 1,3-selenazole scaffolds

Several straightforward and practical processes have been established for the construction of 2-aminothiazoles, 1,3-thiazoles and 1,3-selenazoles from aryliodoazides. These strategies successfully proceed with a wide spectrum of substituted thioamides and its derivatives producing the resulting five-membered heterocycles obtained in satisfactory yields. The unique features of these protocols are operational simplicity and highly functional group tolerance, which make them convenient and practical routes for the preparation of various libraries of 2-aminothiazoles, 1,3-thiazoles, and 1,3-selenazoles.

2-Amino-4-arylthiazoles through One-Pot Transformation of Alkylarenes with NBS and Thioureas

Treatment of alkylarenes with N-bromosuccinimide in a mixture of ethyl acetate and water at 60 °C, a mixture of acetonitrile and water at 80 °C, or a mixture of diethyl carbonate and water under irradiation with a tungsten lamp, followed by a reaction with thioureas or arenethioamides provided the corresponding 2-amino- 4-arylthiazoles or 2,4-diarylthiazoles in good to moderate yields, respectively, in one pot. The present reaction is an efficient one-pot transformation method of alkylarenes into 2-amino-4-arylthiazoles and 2,4-diarylthiazoles directly under mild and transition-metal-free conditions.

Preparation method of 2-aryl-4-alkyl thiazole compound

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Programmed synthesis of arylthiazoles through sequential C-H couplings

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A facile and eco-friendly synthesis of diarylthiazoles and diarylimidazoles in water

A simple, efficient and high yielding greener protocol for the synthesis of substituted thiazoles and imidazoles is described that utilizes the reaction of readily available α-tosyloxy ketones with variety of thioamides/amidines in water.