10243-15-9

Usage

Uses

Used in Pharmaceutical Industry:
3-BROMO-2-METHYL-BENZO[B]THIOPHENE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique molecular structure allows for the creation of new drug molecules with potential therapeutic applications.
Used in Agrochemical Industry:
3-BROMO-2-METHYL-BENZO[B]THIOPHENE is used as a chemical intermediate in the development of agrochemicals, such as pesticides and herbicides. Its reactivity and structural properties make it a valuable component in the synthesis of these compounds, which are designed to protect crops and enhance agricultural productivity.
Used in Organic Synthesis:
3-BROMO-2-METHYL-BENZO[B]THIOPHENE is used as a key building block in the synthesis of complex organic molecules. Its presence of bromine, sulfur, and a methyl group provides a versatile platform for further chemical reactions, enabling the creation of a wide range of organic compounds with diverse applications.

InChI:InChI=1/C9H7BrS/c1-6-9(10)7-4-2-3-5-8(7)11-6/h2-5H,1H3

Upstream product

• 1195-14-8 2-Methylbenzothiophene 
• 6287-82-7 2,3-dibromobenzo[b]thiophene 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 95-15-8 Benzo[b]thiophene 

Downstream Products

• 137814-07-4 1,2-bis(2-methyl-1-benzothiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopent-1-ene 
• 4923-91-5 2,3-dimethylbenzothiophene 
• 57642-62-3 2-methyl-3-phenylbenzothiophen 
• 321584-08-1 1-(5-{4-[bis(4-methylphenyl)amino]phenyl}-2-methylthiophen-3-yl)-2-(2-methylbenzo[b]thiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopentene 
• 1344734-27-5 C₂₅H₁₆F₆S₂ 
• 1195-14-8 2-Methylbenzothiophene 
• 137814-10-9 3,3’-(perfluorocyclobut-1-ene-1,2-diyl)bis(2-methylbenzo[b]thiophene) 
• 1344734-18-4 1-[2-methyl-5-(4-formylphenyl)-3-thienyl]-2-(2-methyl-3-benzothiophenyl) perfluorocyclopentene 

Relevant academic research and scientific papers

Thieme Chemistry Journal Awardees - Where are They Now? The Influence of Electron-Withdrawing Groups at the 2- and 2′-Positions of Dibenzothienylethenes on Molecular Switching

Three dibenzothienylethenes that carry a methyl, a trifluoromethyl, or a fluoro substituent in the 2- and 2′-position were synthesised in short multistep syntheses, respectively. The trifluoromethyl and fluoromethyl substituents significantly improve the absorption properties of the corresponding open and closed isomers (both in the UV-A and in the visible range). The increasing electron deficiency (i) enlarges the portion of the closed and coloured diarylethene isomer in the corresponding photostationary states and slows down the closing and opening isomerisation, (ii) the switching reactions, both closing and opening, are slowed down, and (iii) the switching quantum yields are lowered.

Metal-directed synthesis of quadruple-stranded helical Eu(iii) molecular switch: A significant improvement in photocyclization quantum yield

The self-assembly of a quadruple-stranded Eu(iii) helicate induces the conformation transformation of a DAE-based photochromic ligand from parallel to antiparallel, which brings a significant improvement in the photocyclization quantum yield (Φo-c) as compared with the free ligand. Furthermore, the photocontrolled open- and closed-rings of the ligand realized a reversible modulation toward Eu3+ center emission.

Diastereoselective self-assembly of a triple-stranded europium helicate with light modulated chiroptical properties

Chiroptical photoswitches are of increasing interest for their potential in advanced information technologies. Herein, an achiral bis-β-diketonate ligand (o-L) with a photoresponsive diarylethene moiety as a linker was designed, which co-assembled with Eu3+ions andR- andS-bis(diphenylphosphoryl)-1,10-binaphthyl (R/S-BINAPO) as chiral ancillaries to form dinuclear triple-stranded helicates, [Eu2(o-L)3(R/S-BINAPO)2]. The helicates in the enantiopure form were confirmed by1H,19F,31P NMR and DOSY NMR analyses. Furthermore, the mirror-image CD and CPL spectra also demonstrate the existence of stable ground- and excited-state chiralities in solution. When exposed to alternate ultraviolet and visible light, the helicates showed reversible color variations from colorless to purple, followed by the presence of light-triggered quadruple optical and chiroptical outputs, named CD, PL, CPL andglumswitches. With these light-modulated optical outputs, the possibility for the fabrication of IMPLICATION and INHIBIT logic gates was discussed.

Photomobile polymer materials: Photoresponsive behavior of cross-linked liquid-crystalline polymers with mesomorphic diarylethenes

Cross-linked liquid-crystalline (LC) polymers with a mesomorphic diarylethene were prepared to demonstrate a versatile strategy for cross-linked photochromic LC polymers as photomobile materials. Upon exposure to UV light to cause photocyclization of the diarylethene chromophore, the cross-linked polymer films bend toward an actinic light source. By irradiation with visible light to cause a closed-ring to open-ring isomerization, the bent films revert to the initial flat state. Without visible-light irradiation, the bent films remain bent even at 120 8C, indicating high thermal stability of the cross-linked diarylethene LC polymers.

Reversible Photomodulation of Electronic Communication in a π-Conjugated Photoswitch-Fluorophore Molecular Dyad

The extent of electronic coupling between a boron dipyrromethene (BODIPY) fluorophore and a diarylethene (DAE) photoswitch has been modulated in a covalently linked molecular dyad by irradiation with either UV or visible light. In the open isomer, both moieties can be regarded as individual chromophores, while in the closed form the lowest electronic (S0→S1) transition of the dyad is slightly shifted, enabling photomodulation of its fluorescence. Transient spectroscopy confirms that the dyad behaves dramatically different in the two switching states: while in the open isomer it resembles an undisturbed BODIPY fluorophore, in the closed isomer no fluorescence occurs and instead a red-shifted DAE behavior prevails.

The effects of heteroaryl ring on the photochromism of diarylethenes with a naphthalene moiety

Three new asymmetrical naphthalene-containing diarylethenes with different heteroaryl groups have been synthesized to investigate the heteroaryl effects on their properties. The three diarylethenes exhibited distinctive photochromism with good thermal stability, which may be attributed to the different heteroaryl effects. Their cycloreversion quantum yields increased in the order of 2-methylbenzofuran 2-methylbenzothiophene 1,2-dimethylindole, while the cyclization quantum yields exhibited a reverse trend. Compared to indole and benzothiophene, the benzofuran moiety could effectively shift the absorption maximum to a shorter wavelength and notably enhance the cyclization quantum yield and fluorescence quantum yield of the diarylethene. The results indicated that the category of heteroaryl groups played a vital role during the process of photoisomerization of naphthalene-containing diarylethene derivatives.

Nonsymmetrical 3,4-dithienylmaleimides by cross-coupling reactions with indium organometallics: Synthesis and photochemical studies

The synthesis and photochemical study of novel nonsymmetrical 1,2-dithienylethenes (DTEs) with a maleimide bridge have been carried out. The synthetic approach to the DTEs was based on successive selective palladium-catalyzed cross-coupling reactions of 5-susbtituted-2-methyl-3-thiophenyl indium reagents with 3,4-dichloromaleimides. The required organoindium reagents were prepared from 2-methyl-3,5-dibromothiophene by a selective (C-5) coupling reaction with triorganoindium compounds (R3In) and subsequent metal-halogen exchange. The coupling reactions usually gave good yields and have a high atom economy with substoichiometric amounts of R3In. The results of photochemical studies show that these novel dithienylmaleimides undergo a photocyclization reaction upon irradiation in the UV region and a photocycloreversion after excitation in the visible region, thus they can be used as photochemical switches. ON-OFF operations can be repeated in successive cycles without appreciable loss of effectiveness in the process.

Substituent effects on the photochromic properties of benzothiophene-based derivatives

Five diarylethene photochromic derivatives, the structures of which incorporate a central benzothiophene unit, a left-hand thiazole group, and a right-hand benzothiophene group, have been prepared. The compound with a thiazole unit with no substituent on the reaction-center carbon atom reveals an unprecedented transformation upon light irradiation. When the 4-position of thiazole is protected by a methyl group, the compounds show high photosensitivity and photochromic properties. In this case, light irradiation affords new compounds with [5]helicene structures featuring the highest redshifted absorption maxima reported to date.

5-HETEROARYL-PYRIDIN-2-AMINE CONFOUNDS AS NEUROPEPTIDE FF RECEPTOR ANTAGONISTS

The present invention relates to novel aminopyridine derivatives of the general formula (I) and pharmaceutical compositions comprising these compounds, as well as their therapeutic use, particularly as neuropeptide FF (NPFF) receptor antagonists, including, e.g., for the treatment or prevention of pain, opioid-induced hyperalgesia, or addiction.

Sensitive Assays by Nucleophile-Induced Rearrangement of Photoactivated Diarylethenes

Upon light-induced isomerization, diarylethenes (DAEs) equipped with reactive aldehyde moieties rearrange selectively in the presence of amines, accompanied by decoloration. In a comprehensive study, the probe structure was optimized with regard to its inherent reactivity in the nucleophile-triggered rearrangement reaction. Detailed structure-reactivity relationships could be derived, in particular with regard to the type of integrated (het)aryl moieties as well as the location of the formyl residue, and the probes' intrinsic reactivity with primary and secondary amines was optimized. Utilizing an ancillary base, the initially formed rearrangement product can engage in a subsequent catalytic cycle, leading to an amplified decoloration process. This additional catalytic pathway allows us to enhance the sensitivity of our method and successfully discriminate between amines and thiols. Moreover, probes that exhibit strong analyte-induced fluorescence modulation have been designed to further decrease the detection limit by using a more sensitive read-out. The optimized DAE probes are promising molecular components for future programmable sensing materials and devices.