131106-70-2

Basic information

• Product Name: 6-TRIFLUOROMETHYLBENZOTHIAZOLE
• Synonyms: 6-TRIFLUOROMETHYLBENZOTHIAZOLE;Benzothiazole, 6-(trifluoromethyl)- (9CI);6-(TrifluoroMethyl)benzo[d]thiazole
• CAS NO: 131106-70-2
• Molecular Formula: C₈H₄F₃NS
• Molecular Weight: 203.18
• Product Categories: BENZOTHIAZOLE
• Mol File: 131106-70-2.mol

Chemical Properties

• Melting Point: 42 °C
• Boiling Point: 236.1±35.0 °C(Predicted)
• Appearance: /
• Density: 1.453±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -0.57±0.10(Predicted)
• CAS DataBase Reference: 6-TRIFLUOROMETHYLBENZOTHIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-TRIFLUOROMETHYLBENZOTHIAZOLE(131106-70-2)
• EPA Substance Registry System: 6-TRIFLUOROMETHYLBENZOTHIAZOLE(131106-70-2)

Safety Data

• Hazardous Substances Data: 131106-70-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Trifluoromethylbenzothiazole is used as a key intermediate in the synthesis of various pharmaceuticals for its antimicrobial, antifungal, and antitumor properties, contributing to the development of new drugs with enhanced therapeutic effects.
Used in Agrochemical Industry:
In the agrochemical sector, 6-Trifluoromethylbenzothiazole is utilized as an intermediate in the production of agrochemicals, leveraging its antimicrobial and antifungal properties to create effective solutions for crop protection and disease management.
Used in Materials Science:
6-Trifluoromethylbenzothiazole is employed in materials science as a building block for the development of high-performance polymers and functional materials, capitalizing on its unique chemical structure and properties to engineer advanced materials with specific applications.
Although the exact uses and applications of 6-Trifluoromethylbenzothiazole are still under ongoing research and development, its potential as a versatile compound in multiple industries is evident, promising a valuable role in the creation of innovative products and solutions.

Upstream product

• 455-14-1 4-trifluoromethylphenylamine 
• 95-16-9 1,3-Benzothiazole 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 777-12-8 2-amino-6-trifluoromethyl-1,3-benzothiazole 
• 110-46-3 isopentyl nitrite 

Downstream Products

• 96232-04-1 2-amino-5-trifluoromethylbenzenethiol hydrochloride 
• 943447-83-4 6-trifluoromethyl-2-benzothiazolyltriphenylsilane 
• 1300105-94-5 2-phenylthio-6-trifluoromethyl-1,3-benzothiazole 
• 611-70-1 phenyl isopropyl ketone 
• 1314518-69-8 C₅₄H₅₀F₆N₆O₂S₂ 
• 1314518-77-8 C₅₄H₄₈B₂F₁₀N₆O₂S₂ 
• 86691-07-8 2-amino-5-(trifluoromethyl)benzenethiol 

Relevant articles and documents

Photoelectrochemical cross-dehydrogenative coupling of benzothiazoles with strong aliphatic C-H bonds

A photoelectrochemical strategy for the cross-dehydrogenative coupling of unactivated aliphatic hydrogen donors (e.g.alkanes) with benzothiazoles is reported. We used tetrabutylammonium decatungstate as the photocatalyst to activate strong C(sp3)-H bonds in the chosen substrates, while electrochemistry scavenged the extra electrons.

Iron-catalyzed tandem oxidative coupling and acetal hydrolysis reaction to prepare formylated benzothiazoles and isoquinolines

The aldehyde group is one of the most versatile intermediates in synthetic chemistry, and the introduction of an aldehyde group into heteroarenes is important for the transformation of molecular structure. Herein, we achieved the direct formylation of benzothiazo/les and isoquinolines. The reaction features a novel iron-catalyzed Minisci-type oxidative coupling process using commercially available 1,3-dioxolane as a formylated reagent followed by acetal hydrolysis without a separation process. The reaction can be performed under exceedingly mild reaction conditions and exhibits broad functional group tolerance.

2-AMINOPYRIMIDINE DERIVATIVE, PREPARATION METHOD AND USE THEREOF

The disclosure provides an aminopyrimidine derivative for preventing and treating diseases related to IDH mutation, a preparation method and use thereof. Specifically, the disclosure provides a compound of Formula I, a stereoisomer, racemate thereof, or pharmaceutically acceptable salt thereof. The compound of the general Formula I has isocitrate dehydrogenase 1 (IDH1) inhibitory activity and can treat cancer induced by IDH1 mutation.

Discovery of new small molecule inhibitors targeting isocitrate dehydrogenase 1 (IDH1) with blood-brain barrier penetration

Isocitrate dehydrogenase 1 (IDH1), which catalyzes the conversion of isocitrate to α-ketoglutarate, is one of key enzymes in the tricarboxylic acid cycle (TCA). Hotspot mutation at Arg132 in IDH1 that alters the function of IDH1 by further converting the α-ketoglutarate(α-KG) to 2-hydroxyglutarate (2-HG) have been identified in a variety of cancers. Because the IDH1 mutations occur in a significant portion of gliomas and glioblastomas, it is important that IDH1 inhibitors have to be brain penetrant to treat IDH1-mutant brain tumors. Here we report the efforts to design and synthesize a novel serial of mutant IDH1 inhibitors with improved activity and the blood-brain barrier (BBB) penetration. We show that compound 5 exhibits good brain exposure and potent 2-HG inhibition in a HT1080-derived mouse xenograft model, which makes it a potential preclinical candidate to treat IDH1-mutant brain tumors.

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.

ARYL RECEPTOR MODULATORS AND METHODS OF MAKING AND USING THE SAME

The present invention is generally directed towards compounds capable of binding the aryl hydrocarbon receptor and modulating its activity,methods of treating inflammatory conditions such as Crohn's disease using such compounds, and pharmaceutical compositions comprising such compounds. Also provided are methods of increasing levels of IL-22 in a subject and/or decreasing levels of IFN-γ in a subject.

Pyrrolopyrrole cyanines: Effect of substituents on optical properties

To tune their optical properties, a large variety of pyrrolopyrrole cyanines (PPCys) were synthesized with substitutedheteroaromatics such as quinoline, benzothiazole, and oxazole derivatives as terminal groups. Thus, a broad range of stable, highly fluorescing near-infrared (NIR) dyes with high absorptivities between 690 to 845 nm is accessible. The large number of newly synthesized compounds allows a detailed discussion of the correlation between molecular structure and the optical properties of the first electronic transition. Syntheses and optical properties of pyrrolopyrrole cyanines (PPCys) with different substituents at the terminal heteroaromatic moieties are described. The relationship between molecular structure and optical properties is discussed. By suitable substitution, the absorption and fluorescence maxima of the chromophore can be tuned in a range between 690 and 845 nm. Copyright

Novel, potent aldose reductase inhibitors: 3,4-dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl]methyl]-1- phthalazineacetic acid (zopolrestat) and congeners

A new working hypothesis that there is a hitherto unrecognized binding site on the aldose reductase (AR) enzyme with strong affinity for benzothiazoles was pursued for the design of novel, potent aldose reductase inhibitors (ARIs). The first application of this hypothesis led to a novel series of 3,4-dihydro-4-oxo-3-(benzothiazolylmethyl)-1-phthalazineacetic acids. The parent of this series (207) was a potent inhibitor of AR from human placenta (IC50 = 1.9 x 10-8 M) and was orally active in preventing sorbitol accumulation in rat sciatic nerve, in an acute test of diabetic complications (ED50 = 18.5 mg/kg). Optimization of this lead through medicinal chemical rationale, including analogy from other drug series, led to more potent congeners of 207 and culminated in the design of 3,4-dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl]methyl]-1- phthalazineacetic acid (216, CP-73,850, zopolrestat). Zopolrestat was found to be more potent than 207, both in vitro and in vivo. Its IC50 against AR and ED50 in the acute test were 3.1 x 10-9 M and 3.6 mg/kg, respectively. Its ED50s in reversing already elevated sorbitol accumulation in rat sciatic nerve, retina, and lens in a chronic test were 1.9, 17.6, and 18.4 mg/kg, respectively. It was well absorbed in diabetic patients, resulting in high blood level, showed a highly favorable plasma half-life (27.5 h), and is undergoing further clinical evaluation. An assortment of synthetic methods used for the construction of benzothiazoles, including an efficient synthesis of zopolrestat, is described. Structure-activity relationships in the new series are discussed.