134384-31-9

Basic information

• Product Name: 2-(4-Trifluoromethyl-phenyl)-benzothiazole
• Synonyms: 2-(4-Trifluoromethyl-phenyl)-benzothiazole
• CAS NO: 134384-31-9
• Molecular Formula: C₁₄H₈F₃NS
• Molecular Weight: 279.28
• Mol File: 134384-31-9.mol

Chemical Properties

• Melting Point: 161-162 °C
• Boiling Point: 355.8±52.0 °C(Predicted)
• Appearance: /
• Density: 1.362±0.06 g/cm3(Predicted)
• PKA: 0.09±0.10(Predicted)
• CAS DataBase Reference: 2-(4-Trifluoromethyl-phenyl)-benzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Trifluoromethyl-phenyl)-benzothiazole(134384-31-9)
• EPA Substance Registry System: 2-(4-Trifluoromethyl-phenyl)-benzothiazole(134384-31-9)

Safety Data

• Hazardous Substances Data: 134384-31-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry Research:
2-(4-Trifluoromethyl-phenyl)-benzothiazole is used as a research compound for studying its chemical properties and potential applications in the field of organic chemistry.
Used in Pharmaceutical Development:
2-(4-Trifluoromethyl-phenyl)-benzothiazole is used as a potential anti-tumor agent for its biological activity, indicating its use in the development of pharmaceuticals for cancer treatment.
Used as a Fluorescent Probe:
In Analytical Chemistry, 2-(4-Trifluoromethyl-phenyl)-benzothiazole is used as a fluorescent probe for detecting metal ions, which is crucial for environmental and biological monitoring.
Used in Materials Science:
2-(4-Trifluoromethyl-phenyl)-benzothiazole is used in the development of organic light-emitting diodes (OLEDs) and other electronic devices, leveraging its fluorescent properties for advanced material applications.
Used in the Development of Electronic Devices:
In the Electronics Industry, 2-(4-Trifluoromethyl-phenyl)-benzothiazole is utilized for its potential in enhancing the performance of electronic devices, particularly in the area of display and lighting technologies.

Upstream product

• 95-16-9 1,3-Benzothiazole 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 455-18-5 4-CF₃C₆H₄CN 
• 137-07-5 2-amino-benzenethiol 
• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 
• 3300-51-4 p-Trifluoromethylbenzylamine 
• 98-95-3 nitrobenzene 
• 62-53-3 aniline 
• 79478-02-7 4-(trifluoromethyl)phenylglyoxylic acid 
• 1155-00-6 bis(2-nitrophenyl)disulfide 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 615-36-1 2-bromoaniline 
• 1017041-20-1 C₁₄H₉BrF₃NO 
• 6140-17-6 4-methylbenzotrifluoride 

Relevant articles and documents

Iron(ii)-catalyzed sulfur directed C(sp3)-H bond amination/C-S cross coupling reaction

An efficient iron(ii)-catalyzed sulfur directed C(sp3)-H bond amination/C-S cross coupling reaction has been developed. The reaction had high tolerance of functional groups under moderate conditions. The results of a deuterium labeling study and in situ ESI-MS experiments indicated that the reaction mechanism probably corresponds to a Fe(ii)/Fe(iii) catalytic cycle.

Well-Defined N-Heterocyclic Carbene-Palladium Complexes as Efficient Catalysts for Domino Sonogashira Coupling/Cyclization Reaction and C-H bond Arylation of Benzothiazole

Well-defined and air-stable PEPPSI (Pyridine Enhanced Precatalyst Preparation Stabilization and Initiation) themed palladium bis-N-heterocyclic carbene complexes have been developed for the domino Sonogashira coupling/cyclization reaction of 2-iodophenol with a variety of terminal alkynes and C-H bond arylation of benzothiazole with aryl iodides. The PEPPSI themed palladium complexes, 2a and 2b were synthesized in good yields from the reaction of corresponding imidazolium salts with PdCl2 and K2CO3 in pyridine. The new air-stable palladium-NHC complexes were characterized by NMR spectroscopy, X-ray crystallography, elemental analysis, and mass spectroscopy studies. The PEPPSI themed palladium(II) bis-N-heterocyclic carbene complexes 2a and 2b exhibited excellent catalytic activities for domino Sonogashira coupling/cyclization reaction of 2-iodophenol with terminal alkynes yielding benzofuran derivatives. In addition, the palladium complexes, 2a and 2b successfully catalyzed the direct C-H bond arylation of benzothiazole with aryl iodides as coupling partners in presence of CuI as co-catalyst.

Catalyst-Free Synthesis of 2-Arylbenzothiazoles in an Air/DMSO Oxidant System

A straightforward strategy for the synthesis of 2-arylbenzothiazoles from 2-aminothiophenol and aryl aldehydes in air/DMSO oxidant system has been developed. This reaction is operationally simple, proceeds without catalysts, tolerates a wide range of func

Synthesis of 2-Arylbenzothiazoles from Nitrobenzenes, Benzylamines, and Elemental Sulfur via Redox Cyclization

A sustainable advanced synthetic method was developed based on redox cyclization for the synthesis of 2-arylbenzothiazoles in good to excellent yields from readily available nitrobenzenes, benzylamines, and elemental sulfur without the use of transition-metal catalysts. This method is remarkable: nitro group reduction, a benzylamine redox reaction, sulfuration, condensation, and cyclization, all proceed in a single step to generate a heterocycle. It is also highly atom-economical and does not require any external oxidizing or reducing agents.

Graphene oxide-catalyzed synthesis of benzothiazoles with amines and elemental sulfur via oxidative coupling strategy of amines to imines

The graphene oxide-catalyzed coupling and cyclization reactions of primary amines with elemental sulfur was developed to afford various optically property benzothiazoles. This coupling and cyclization strategies proceeded under the oxidant system graphene oxide/O2 and constructed carbon-heteroatom (N, S) bonds with amines and elemental sulfur. Due to benzothiazoles as common chromophores, these products exhibited intriguing fluorescence properties, including outstanding Stokes shifts (up to 161 nm) and quantum yields (up to 74%). Utilizing the products’ unique fluorescence response in different solvents, β-naphthothiazole 4a showed excellent aggregation-induced emission properties in 1,2-dichloroethane, which was 60 times higher than in tetrahydrofuran.

Inkable CF3-functionalized benzothiazole/benzimidazole-Ir(III) complexes for efficient bilayer-inkjet-printed OLEDs

The inkjet-printed organic light-emitting diodes (OLEDs) are gradually gaining popularity due to their low cost, free vacuum environment, patterning, and large-area display capability, but inkable phosphors are yet less reported. In order to develop inkab

Room temperature HFIP/Ag-promoted palladium-catalyzed C–H functionalization of benzothiazole with iodoarenes

A versatile synthetic protocol involving the room temperature direct arylation of benzothiazole with a wide variety of iodoarenes under Ag-promoted Pd-catalyzed conditions in HFIP as the reaction solvent has been presented. A sequential HFIP-promoted sele

ZnO-NPs catalyzed condensation of 2-aminothiophenol and aryl/alkyl nitriles: Efficient green synthesis of 2-substituted benzothiazoles

The synthesis of 2-substituted benzothiazoles has been described using ZnO-nanoparticles as a catalyst. The condensation of 2-aminothiophenol and aryl/alkyl nitriles resulted in the formation of various 2-substituted benzothiazoles under solvent-free reaction conditions. The library of 2-substituted benzothiazoles has been synthesized in good to excellent yield. The reaction has shown a wide range of functional group compatibility for both varyingly substituted 2-aminothiophenols and nitriles. The protocol has many advantages such as faster reaction rate, mild reaction conditions, various functional group compatibility, excellent yield, solvent-free reaction conditions, easy recovery of materials, and excellent catalyst recyclability, among others. The various advantages of this protocol make it a more feasible, economical, and environmentally benign process.

α-Keto Acids as Triggers and Partners for the Synthesis of Quinazolinones, Quinoxalinones, Benzooxazinones, and Benzothiazoles in Water

A general and efficient method for the synthesis of quinazolinones, quinoxalinones, benzooxazinones, and benzothiazoles from the reactions of α-keto acids with 2-aminobenzamides, benzene-1,2-diamines, 2-aminophenols, and 2-aminobenzenethiols, respectively, is described. The reactions were conducted under catalyst-free conditions, using water as the sole solvent with no additive required, and successfully applied to the synthesis of sildenafil. More importantly, these reactions can be conducted on a mass scale, and the products can be easily purified through filtration and washing with ethanol (or crystallized).

Sulfur-Promoted Redox Cyclization of 2,2′-Dinitrodiphenyl Disulfides and Benzylamines

This study aims to develop green and sustainable advanced synthetic methods based on redox cyclization. Elemental sulfur is shown to promote the efficient synthesis of 2-substituted benzothiazoles from 2,2′-dinitrodiphenyl disulfides and benzylamines via redox cyclization in the absence of transition-metal catalysts and solvents. The 2-substituted benzothiazoles are obtained in good to excellent yields. This synthetic methodology is highly atom-economical and does not require any external oxidizing and/or reducing agents.