14468-40-7

Usage

Uses

Used in Organic Synthesis:
2-(Trifluoromethyl)benzothiazole is utilized as a building block in organic synthesis for the preparation of a variety of functionalized molecules. Its unique structure allows for the creation of compounds with potential biological activities, making it a valuable component in the synthesis of pharmaceuticals and other bioactive substances.
Used in Pharmaceutical Research:
In pharmaceutical research, 2-(Trifluoromethyl)benzothiazole serves as a key intermediate for developing new drugs. Its incorporation into molecular structures can enhance the pharmacological properties of the resulting compounds, contributing to the discovery of novel therapeutic agents.
Used in Materials Science:
2-(Trifluoromethyl)benzothiazole has been investigated for its potential applications in materials science. Its unique properties may contribute to the development of advanced materials with specific characteristics required for various high-tech applications.
Used as a Fluorescent Probe for Detecting Metal Ions:
2-(Trifluoromethyl)benzothiazole has also been explored for its use as a fluorescent probe for detecting metal ions. Its ability to interact with metal ions and exhibit fluorescence upon binding makes it a potentially useful tool in analytical chemistry and environmental monitoring for the detection and quantification of metal contaminants.

InChI:InChI=1/C5H3Cl2NO2S/c6-5-4(11(7,9)10)2-1-3-8-5/h1-3H

Upstream product

• 137-07-5 2-amino-benzenethiol 
• 76-05-1 trifluoroacetic acid 
• 75092-43-2 cis-1,1,1,5,5,5-hexafluoro-4-hydroxy-3-penten-2-one 
• 119197-24-9 3-chloro-4,4,4-trifluoro-2-phenyl-but-2-enal 
• 135106-04-6 3-chloro-4,4,4-trifluoro-1-phenyl-2-buten-1-one 
• 239437-47-9 3,3,4,4,4-Pentafluoro-butyraldehyde 
• 61881-11-6 2,2,2-trifluoro-N-phenylethanethioamide 
• 1160967-80-5 2,2,2-trifluoro-N-(2-iodophenyl)acetimidoyl chloride 
• 1087794-62-4 N-(2-chlorophenyl)-2,2,2-trifluoroethanimidoyl chloride 
• 61881-19-4 2,2,2-trifluoro-N-phenyl-acetimidoyl chloride 
• 95-16-9 1,3-Benzothiazole 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 136-95-8 2-amino-benzthiazole 
• 75-90-1 2,2,2-Trifluoroacetaldehyde 

Relevant academic research and scientific papers

One-pot synthesis of 2-trifluoromethyl and 2-difluoromethyl substituted benzo-1,3-diazoles

2-Trifluoromethyl and 2-difluoromethyl substituted benzimidazole, benzoxazole and benzothiazole derivatives were efficiently prepared through a one-pot reaction of trifluoroacetic acid and difluoroacetic acid, respectively, with commercially available o-p

Recyclable copper-catalyzed cyclization of o-haloanilides and metal sulfides: An efficient and practical access to substituted benzothiazoles

An efficient heterogeneous copper-catalyzed cyclization of o-haloanilides and metal sulfides has been achieved via the C–S coupling in DMF at 80 or 140 °C in the existence of an MCM-41-bound NHC-Cu(I) catalyst and then intramolecular condensation, delivering a wide range of substituted benzothiazoles in mostly good to high yields. This new MCM-41-NHC-CuI complex can facilely be obtained by a two-step procedure starting from easily accessible and inexpensive reagents and reused more than seven times without any significant loss of its catalytic efficiency. The present protocol has been successfully applied to the gram-scale synthesis of two antitumor agents 5F203 and PMX 610.

Metallaphotoredox Perfluoroalkylation of Organobromides

Ruppert-Prakash type reagents (TMSCF3, TMSC2F5, and TMSC3F7) are readily available, air-stable, and easy-to-handle fluoroalkyl sources. Herein, we describe a mild, copper-catalyzed cross-coupling of these fluoroalkyl nucleophiles with aryl and alkyl bromides to produce a diverse array of trifluoromethyl, pentafluoroethyl, and heptafluoropropyl adducts. This light-mediated transformation proceeds via a silyl-radical-mediated halogen atom abstraction pathway, which enables perfluoroalkylation of a broad range of organobromides of variable steric and electronic demand. The utility of the method is demonstrated through the late-stage functionalization of several drug analogues.

Cathodic C-H Trifluoromethylation of Arenes and Heteroarenes Enabled by an in Situ-Generated Triflyltriethylammonium Complex

While several trifluoromethylation reactions involving the electrochemical generation of CF3 radicals via anodic oxidation have been reported, the alternative cathodic, reductive radical generation has remained elusive. Herein, the first cathodic trifluoromethylation of arenes and heteroarenes is reported. The method is based on the electrochemical reduction of an unstable triflyltriethylammonium complex generated in situ from inexpensive triflyl chloride and triethylamine, which produces CF3 radicals that are trapped by the arenes on the cathode surface.

A radical approach to the copper oxidative addition problem: Trifluoromethylation of bromoarenes

Transition metal–catalyzed arene functionalization has been widely used for molecular synthesis over the past century. In this arena, copper catalysis has long been considered a privileged platform due to the propensity of high-valent copper to undergo reductive elimination with a wide variety of coupling fragments. However, the sluggish nature of oxidative addition has limited copper’s capacity to broadly facilitate haloarene coupling protocols. Here, we demonstrate that this copper oxidative addition problem can be overcome with an aryl radical–capture mechanism, wherein the aryl radical is generated through a silyl radical halogen abstraction. This strategy was applied to a general trifluoromethylation of aryl bromides through dual copper-photoredox catalysis. Mechanistic studies support the formation of an open-shell aryl species.

RODENTIA ANIMAL REPELLENT

PROBLEM TO BE SOLVED: To provide a repellent having a superior repellent activity for Rodentia animals, and a repellent method for Rodentia animals. SOLUTION: A Rodentia animal repellent contains, as an active ingredient, a compound represented by the for

Metal-free synthesis of benzothiazoles from disulfides of 2-aminobenzenethiol and carboxylic acid via PCl3-promoted tandem reaction

A metal-free process for the synthesis of benzothiazoles via PCl3-promoted cleavage/acylation/ cyclization of disulfides and carboxylic acids has been developed. In addition to acting as the acylating reagent which converted carboxylic acids into acyl chlorides, PCl3 also converted disulfides to thiols, which promoted disulfides of 2-aminobenzenethiol reacted with carboxylic acid to produce benzothiazoles. The developed method is applicable to a wide range of carboxylic acids containing different functional groups.

FeCl3/ultrasound mediated reaction of 2-aminothiophenol with aldehydes in water: Synthesis of 2-substituted benzothiazoles of pharmacological interest

We report a FeCl3?6H2O mediated green and rapid access to benzothiazole derivatives having a substituent at C-2 via the condensation of 2-aminothiophenol with various aldehydes under ultrasound irradiation and air. The reaction progressed well in water affording the expected products in good yields. Two of these compounds known to be potent anticancer agents showed good interactions with PDE4B in silico and inhibited this enzyme when tested in vitro.

RODENTIA ANIMAL REPELLENT

Provided are a repellent having a superior repellent activity for Rodentia animal and a repellent method for Rodentia animal. A Rodentia animal repellent containing, as an active ingredient, a compound represented by the formula (1) wherein Z1

One-pot sandmeyer trifluoromethylation and trifluoromethylthiolation

Practical one-pot procedures were developed for both Sandmeyer-type trifluoromethylations and trifluoromethylthiolations. Starting from broadly available (hetero)aromatic amines, various benzotrifluorides were synthesized in high yields via in situ diazotization and copper-mediated trifluoromethylation using the inexpensive Ruppert-Prakash trifluoromethylating reagent. In the presence of sodium thiocyanate as a sulfur source, aryl trifluoromethyl thioethers are exclusively formed.