6344-17-8

Usage

Uses

Used in Pharmaceutical Applications:
(6E)-6-(1,3-benzothiazol-2(3H)-ylidene)-4-bromocyclohexa-2,4-dien-1-one is used as a potential pharmaceutical agent for [application reason], such as targeting specific biological pathways or exhibiting therapeutic effects. Its unique structure may allow for the development of new drugs with novel mechanisms of action.
Used in Materials Science:
In the field of materials science, (6E)-6-(1,3-benzothiazol-2(3H)-ylidene)-4-bromocyclohexa-2,4-dien-1-one is used as a component in the development of new materials with [specific properties], such as enhanced stability, conductivity, or optical characteristics. Its structural features may contribute to the creation of advanced materials with improved performance.
Used in Organic Synthesis:
(6E)-6-(1,3-benzothiazol-2(3H)-ylidene)-4-bromocyclohexa-2,4-dien-1-one serves as a key intermediate in organic synthesis, used as a building block for the synthesis of more complex molecules with [desired properties or applications]. Its unique structure may facilitate the development of new synthetic routes and methodologies.

Upstream product

• 89-55-4 5-bromosalicyclic acid 
• 137-07-5 2-amino-benzenethiol 
• 1761-61-1 5-bromosalicyclaldehyde 
• 95-16-9 1,3-Benzothiazole 
• 22532-62-3 4-bromosalicylaldehyde 
• 19654-14-9 2-(3-Bromo-phenyl)-benzothiazole 
• 1141-88-4 2-Aminophenyl disulfide 

Downstream Products

• 1351664-94-2 2-[2-(benzyloxy)-5-(2,3,5,6-tetrafluoropyridyl)phenyl]benzothiazole 
• 1351664-95-3 2-[2-(benzyloxy)-5-(2,3,4,5,6-pentafluorophenyl)phenyl]benzothiazole 
• 1351664-96-4 2-[2-(benzyloxy)-5-phenylphenyl]benzothiazole 
• 1351664-97-5 2-{2-(benzyloxy)-5-[4-(dimethylamino)phenyl]phenyl}benzothiazole 
• 1351664-98-6 2-[2-hydroxy-5-(2,3,5,6-tetrafluoropyridyl)phenyl]benzothiazole 
• 1351664-99-7 2-[2-hydroxy-5-(2,3,4,5,6-pentafluorophenyl)phenyl]benzothiazole 
• 145551-25-3 2-(2-hydroxy-5-phenylphenyl)benzothiazole 
• 1351665-00-3 2-{5-[4-(dimethylamino)phenyl]-2-hydroxyphenyl}benzothiazole 
• 1351664-91-9 2-[2-(benzyloxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]benzothiazole 
• 1351664-90-8 2-[2-(benzyloxyl)-5-bromophenyl]benzothiazole 

Relevant academic research and scientific papers

A smart sensor for rapid detection of lethal hydrazine in human blood and drinking water

Hydrazine exposure leads to damage of all vital organs of humans and animals, which demands the discovery of a method for the rapid and quantitative detection of hydrazine. Newly designed and synthesized receptor-bearing phenolic-OH,-Br,-CN,-ester and ben

Fluorescence imaging of surface-versatile latent fingerprints at the second and third level using double ESIPT-based AIE fluorophore

Latent fingerprints (LFPs) identification is of paramount importance for national security and criminal investigations. We designed and synthesized fluorescent organic molecule HPBI for the rapid fluorescence imaging of latent fingerprints on various surfaces such as aluminium foil, currency paper, brick, and glass, which did not require any post treatment. The HPBI exhibits a combination of ESIPT and AIE properties and forms green fluorescent nano-aggregates in CH3CN-H2O (1?:?1) mixture, as evaluated by DFT, SEM, TEM, and fluorescent microscopic studies. Spraying the solution of spherical HPBI nanoaggregates (50-100 nm size) on various surfaces resulted in fluorescence display of LFPs in 2 minutes. LFPs clearly revealed level-2 (ridge ending, islands, bifurcation) and level-3 (ridges path deviation, edge contours, sweat pores) details with high contrast and no background interference. The relocation of fluorescent fingerprints on cello tape provides an efficient and clean method for carrying fingerprints to the forensic laboratory. This journal is

Rational design of the benzothiazole-based fluorescent scaffold for tunable emission

The 2-(2-hydroxyphenyl)-benzothiazole (HBT) fluorophore has attracted considerable attention due to its excited-state intramolecular proton transfer (ESIPT) based emission and its large Stokes shift. However, this fluorophore possesses several disadvantag

Fate of protected HBT based chemodosimeters after undergoing deprotection: Restoration of ESIPT or generation of emissive phenoxide?

The -OH group protected 2-(hydroxyphenyl) benzothiazole (HBT) based ratiometric chemodosimeters have previously been reported to undergo regeneration of excited state intramolecular proton transfer (ESIPT) process upon deprotection. In the current work it is demonstrated for the first time that generation of anion of HBT leads to the optical changes in these types of chemodosimeters rather than regeneration of HBT by using a Hydrazine specific chemodosimeter based on substituted HBT.

Synthesis, characterization, crystal structures, and anticancer activity of some new 2,3-dihydro-1,5-benzoxazepines

Various benzoxazepine derivatives have been synthesized and characterized using IR, NMR, GC–MS, and microanalysis. The single-crystal X-ray structures of 2,2-dimethyl-4-[(E)-2-(4-methylphenyl)ethenyl]-2,3-dihydro-1,5-benzoxazepine (RS01), 4-[(E)-2-(2-chlo

The exquisite integration of ESIPT, PET and AIE for constructing fluorescent probe for Hg(II) detection and poisoning

Excessive mercury ions (Hg2+) in the environment can accumulate in human body along with the food chain to cause serious physiological reactions. The fluorescence probes were considered as convenient tool with great potential for Hg2+ detection. Most existing probes suffer from aggregation-induced quenching (ACQ) effects and insufficient sensitivity. Herein, a novel type of fluorophore was developed by combining the aggregation-induced emission (AIE) and excited state intramolecular proton transfer (ESIPT) characteristics. Subsequently, a phenyl thioformate group with photoinduced electron transfer (PET) effect was connected to give an efficient turn-on probe (HTM), which exhibited good selectivity toward Hg2+, short response time (30 min), coupled with extremely low detection limit (LOD = 1.68 nmol/L). In addition, HTM was used successfully in real samples, cells and drug evaluation, underlying the superiority of HTM to detect Hg2+ in practical applications.

Aerobic oxidative synthesis of quinazolinones and benzothiazoles in the presence of laccase/DDQ as a bioinspired cooperative catalytic system under mild conditions

The current study applied laccase/DDQ as a bioinspired cooperative catalytic system for the synthesis of quinazolinones (80-95% yield) and benzothiazoles (65-98% yield) using air or O2 as ideal oxidants in aqueous media at ambient temperature. The aerobic oxidative cyclization reactions occur in two steps: (i) chemical cyclization; (ii) chemoenzymatic oxidation. These methods are more environment-friendly, efficient, simple and practical than other reported methods due to the use of O2 as an oxidant, laccase as an eco-friendly biocatalyst, aqueous media as the solvent and free from any toxic transition metal and halide catalysts. Therefore, these methods can be applied in pharmaceutical and other sensitive synthetic procedures.

Highly efficient AgNO3-catalyzed approach to 2-(benzo[d]azol-2-yl)phenols from salicylaldehydes with 2-aminothiophenol, 2-aminophenol and benzene-1,2-diamine

A new, convenient and efficient AgNO3-catalyzed strategy for the preparation of 2-(benzo[d]azol-2-yl)phenol derivatives in good to excellent yields (63–98%) is described. The reaction proceeds via condensation/intramolecular nucleophilic addition/oxidation process between substituted salicylaldehydes and 2-aminothiophenol, 2-aminophenol or benzene-1,2-diamine under mild reaction conditions. Notably, this reaction utilizes cheap AgNO3 as a readily available and low-cost benign oxidant at low catalyst loadings with excellent functional group tolerance.

Highly fluorescent response of 4-(2,5-dimethylthiophen-3-yl)-2- hydroxyphenylbenzothiazole toward BF3?Et2O and Zn2+

In this contribution, the emission response of 4-(2,5-dimethylthiophen-3-yl)-2-(2-hydroxy- phenyl)benzothiazole (THBT) was investigated in detail. The experimental shows that Zn2+ could induce fluorescence increasing in tetrahydrofuran (THF). Especially, the quenched emission of THBT was significantly enhanced with 0.76 quantum yield. Due to the coordination of Zn2+, the excited state intramolecular proto transfer (ESIPT) was inhibited and leads to emission quenching correspondingly. The strong emission could ascribe to the Zn-THBT complex. As well, the addition of BF3·Et2O also could form fluorine-boron complex and inhibit ESIPT effect. Additionally, the BF complex is also a strong blue emitter. Therefore, strong blue emission upon BF3·Et2O addition to THBT in dioxane was found. The possible coordinating mechanisms of THBT coordinate with Zn2+ and BF3·Et2O were given.

The excited-state intramolecular proton transfer fluorescence of HBT derivative induced by solvent polarity

In this contribution, a dye (THBT) with 2,5-dimethylthiophene substituted to 2-(2-hydroxyphenyl)benzothiazole was synthesized and characterized by NMR and mass spectroscopic techniques. Its emission behavior in various solvents was investigated and obvious negative solvatochromism was observed. The emission maximum of THBT varied from deep blue (425?nm) in DMSO to orange (550?nm) in chloroform. It is also highly emissive in polycarbonate film and solid powder with the emission peaks 546 and 554?nm, respectively. The ESIPT effect, together with the relaxation of free rotation of thiophene in the excited states, shifted the solid emission 34?nm toward longer wavelength furtherly, with respect the 520?nm (green) emission of HBT. Quantum calculation of frontier molecular orbitals uncovers the underlying mechanism of negative solvatochromism.