1427-09-4

Basic information

• Product Name: 4-(4-FLUORO-PHENYL)-THIAZOL-2-YL]-PHENYL-AMINE
• Synonyms: 4-(4-fluorophenyl)-N-phenyl-1,3-thiazol-2-amine
• CAS NO: 1427-09-4
• Molecular Formula: C₁₅H₁₁FN₂S
• Molecular Weight: 270.33
• Product Categories: pharmacetical
• Mol File: 1427-09-4.mol

Chemical Properties

• Boiling Point: 424.4°Cat760mmHg
• Flash Point: 210.5°C
• Appearance: /
• Density: 1.301g/cm³
• Vapor Pressure: 2.07E-07mmHg at 25°C
• Refractive Index: 1.66
• CAS DataBase Reference: 4-(4-FLUORO-PHENYL)-THIAZOL-2-YL]-PHENYL-AMINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-FLUORO-PHENYL)-THIAZOL-2-YL]-PHENYL-AMINE(1427-09-4)
• EPA Substance Registry System: 4-(4-FLUORO-PHENYL)-THIAZOL-2-YL]-PHENYL-AMINE(1427-09-4)

Safety Data

• Hazardous Substances Data: 1427-09-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-Fluoro-phenyl)-thiazol-2-yl]-phenyl-amine is used as a building block for the synthesis of various pharmaceutical compounds due to its unique structural features. The presence of the thiazole ring and the phenyl-amine group, along with the fluorine atom, may contribute to the compound's biological activity and selectivity, making it a valuable component in the development of new drugs.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 4-(4-Fluoro-phenyl)-thiazol-2-yl]-phenyl-amine serves as a key intermediate in the synthesis of potential drug candidates. Its structural attributes allow for the exploration of various chemical modifications, which can lead to the discovery of novel therapeutic agents with improved pharmacological properties.
Used in Organic Synthesis:
4-(4-Fluoro-phenyl)-thiazol-2-yl]-phenyl-amine is employed as a versatile reagent in organic synthesis, enabling the formation of a wide range of chemical products. Its unique functional groups facilitate various chemical reactions, such as nucleophilic substitution, electrophilic aromatic substitution, and cross-coupling reactions, which can be harnessed to synthesize complex organic molecules with diverse applications.
Used in Drug Discovery:
4-(4-Fluoro-phenyl)-thiazol-2-yl]-phenyl-amine plays a crucial role in drug discovery, where it is used as a starting material or a scaffold for the design of new pharmaceutical agents. Its structural features can be optimized through medicinal chemistry approaches to enhance the compound's potency, selectivity, and pharmacokinetic properties, ultimately leading to the development of more effective and safer drugs.

InChI:InChI=1/C15H11FN2S/c16-12-8-6-11(7-9-12)14-10-19-15(18-14)17-13-4-2-1-3-5-13/h1-10H,(H,17,18)

Upstream product

• 456-04-2 2-Chloro-4'-fluoroacetophenone 
• 103-85-5 monophenylthiourea 
• 896885-34-0 1-(4-fluorophenyl)ethan-1-one-O-acetyl oxime 
• 103-72-0 phenyl isothiocyanate 
• 403-29-2 2-bromo-4'-fluoroacetophenone 
• 357952-79-5 1-(4-fluorophenyl)-2-(p-tolylsulfonyloxy)ethanone 
• 403-42-9 1-(4-fluorophenyl)ethanone 

Relevant articles and documents

Highly efficient heterogeneous copper-catalysed coupling of oxime acetates with isothiocyanates leading to 2-aminothiazoles

The heterogeneous coupling reaction of oxime acetates with isothiocyanates was achieved at 110°C in toluene in air in the presence of a bidentate nitrogen-functionalised MCM-41-immobilised copper(I) complex (MCM-41-2N-CuI) with Cs2CO3 as base to afford a variety of 2-aminothiazoles in good yields. The MCM-41-2N-CuI catalyst can be easily recovered by a simple filtration and reused at least eight times without significant loss of activity.

Copper-Catalyzed Coupling of Oxime Acetates with Isothiocyanates: A Strategy for 2-Aminothiazoles

A new strategy for 2-aminothiazoles is developed via the copper-catalyzed coupling of oxime acetates with isothiocyanates. Various 4-substituted and 4,5-disubstituted 2-aminothiazoles were formed smoothly under mild reaction conditions. This process involved copper-catalyzed N-O bond cleavage, activation of vinyl sp2 C-H bonds, and C-S/C-N bond formations. It is noteworthy that the oxime acetates were used not only as a substrate but also as a single oxidant.

Green approach: An efficient synthesis of 2,4-disubstituted-1,3-thiazoles and selenazoles in aqueous medium under ultrasonic irradiation

An efficient and rapid procedure for the synthesis of 2,4-disubstituted-1,3-thiazoles and selenazoles has been described by the reaction of α-bromoketones with thiourea, phenylthiourea and selenourea at ambient temperature in aqueous medium under ultrasonic irradiation. Analytically pure products were formed within 10-60 s in excellent yields. The advantageous features of this non-conventional methodology over conventional methods are the operational simplicity, easy handling, yield-enhancing, time-reducing, mild reaction conditions and no by-product production.

Effect of substituents on the regioselectivity of the reaction of α-tosyloxyketones with thioureas in acidic medium: Access to 2-aminothiazoles and 2-imino-2,3-dihydrothiazoles

Regioselective condensation of α-tosyloxyacetophenones 1 and N-substituted thioureas 2 in acidic medium to give regioisomers 2-aminothiazoles I and 2-imino-2,3-dihydrothiazoles II is largely influenced by the substituents present on 1 and 2. A mechanism,

Facile one-pot procedure for the synthesis of 2-aminothiazole derivatives

A facile, efficient synthesis of 2-aminothiazole derivatives by the reaction of easily available aromatic methyl ketones with thiourea/N-substituted thioureas in the presence of copper(II) bromide was developed. The reaction underwent a one-pot ?-bromination/cyclization process.

Small molecule library synthesis using segmented flow

Flow chemistry has gained considerable recognition as a simple, efficient, and safe technology for the synthesis of many types of organic and inorganic molecules ranging in scope from large complex natural products to silicon nanoparticles. In this paper

One-pot synthesis of 2-aminothiazoles in PEG-400

A facile one-pot synthesis of 2-aminothiazoles has been carried in PEG-400 as a greener medium at room temperature. This method avoids the use of lachrymatric α-bromoketones as well as the volatile, toxic organic solvents.

Efficient synthesis of 2-aminothiazoles and fanetizole in liquid PEG-400 at ambient conditions

A simple and practical procedure for the synthesis of 2-aminothiazoles from α-tosyloxyketones and thioureas is described using PEG-400[poly(ethylene glycol-400)] at ambient conditions. The developed protocol is successfully applied for the preparation of an anti-inflammatory drug, Fanetizole.

Catalyst-free efficient synthesis of 2-aminothiazoles in water at ambient temperature

A highly efficient and facile method has been described for the synthesis of substituted 2-aminothiazoles in water without any added catalyst or co-organic solvent. The reaction was carried out at ambient temperature and the products were obtained in excellent isolated yields. The developed protocol is successfully applied for the preparation of an anti-inflammatory drug, fanetizole.

The Hantzsch Thiazole Synthesis under Acidic Conditions: Change of Regioselectivity

The condensation of α-halogeno ketones with N-monosubstituted thioureas in neutral solvent leads exclusively to 2-(N-substituted amino)thiazoles.In the present work it was shown that under acidic conditions mixtures of 2-(N-substituted amino)thiazoles and 3-substituted 2-imino-2,3-dihydrothiazoles are formed. (The isomers were distinguished by characteristic differences between their 5-H 1H n.m.r. signals and the i.r.CO bands of their trifluoroacetate derivatives.) The proportions of the 2-imino-2,3-dihydrothiazoles in the mixtures are influenced by experimental features and by the structures of the starting materials.Reactions in 10 M-HCl-EtOH (1:2) at 80 deg C for 20 min were found to be the most efficient for generating 2-imino-2,3-dihydrothiazoles; in the most favourable case 2-imino-3,4-dimethyl-2,3-dihydrothiazole was obtained in 73 percent yield.A possible explanation of the results is discussed.