Category: benzothiophene

Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization was written by Song, Song;Sun, Xiang;Li, Xinwei;Yuan, Yizhi;Jiao, Ning. And the article was included in Organic Letters in 2015.Synthetic Route of C9H7BrS This article mentions the following:

An efficient and practical system for inexpensive bromination and iodination of arenes as well as heteroarenes by using readily available DMSO (DMSO) and HX (X = Br, I) reagents is reported. This mild oxidative system demonstrates a versatile protocol for the synthesis of aryl halides. HX (X = Br, I) are employed as halogenating reagents when combined with DMSO which participates in the present chem. as a mild and inexpensive oxidant. This oxidative system is amenable to late-stage bromination of natural products. The kilogram-scale experiment (>95% yield) shows great potential for industrial application. In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9Synthetic Route of C9H7BrS).

3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9) belongs to benzothiophene derivatives. Benzothiophene is a fused ring compound of thiophene ring and benzene ring, which is an important class of heterocycles with advantageous structures. It has been used as a raw material for the synthesis of biologically active structures and is found in pharmaceuticals such as leukotriene synthesis inhibitors and antifungals, as well as in many natural products.Synthetic Route of C9H7BrS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Unsymmetrical Thienopentalenes: Synthesis, Optoelectronic Properties, and (Anti)aromaticity Analysis was written by Gazdag, Tamas;Mayer, Peter J.;Kalapos, Peter Pal;Holczbauer, Tamas;El Bakouri, Ouissam;London, Gabor. And the article was included in ACS Omega in 2022.Application of 6287-82-7 This article mentions the following:

The synthesis and properties of a series of unsym. thienopentalenes are explored, including both monoareno and diareno derivatives For the synthesis of monoareno pentalenes, a carbopalladation cascade reaction between alkynes and gem-dibromoolefins was applied. Diareno pentalene derivatives were accessed via gold-catalyzed cyclization of diynes. Thiophene was fused to pentalene in two different geometries via its 2,3 and 3,4 bonds. 2,3-Fusion resulted in increased antiaromaticity of the pentalene unit compared to the 3,4-fusion both in the monoareno and diareno framework. Monothienopentalenes that contained the destabilizing 2,3-fusion could not be isolated. For diareno derivatives, the aromatic character of the different aryl groups fused to the pentalene was not independent. Destabilizing fusion on one side resulted in alleviated aromaticity on the other side and vice versa. The synthesized mols. were characterized exptl. by ¹H NMR and UV-vis spectroscopies, cyclic voltammetry, and X-ray crystallog., and their aromatic character was assessed using magnetic (NICS and ACID) and electronic indexes (MCI and FLU). In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Application of 6287-82-7).

2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The core structure is a part of various pharmaceutical substances and natural products. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Application of 6287-82-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Easily-soluble heteroacene bis(benzothieno)silole derivatives for sensing of nitro explosives was written by Zhao, Yunfang;Hao, Wanglong;Ma, Wangjing;Zang, Zhanzhan;Zhang, Huarong;Liu, Xiaoxia;Zou, Sufen;Zhang, Haixia;Liu, Weichao;Gao, Jianhua. And the article was included in New Journal of Chemistry in 2014.Electric Literature of C8H4Br2S This article mentions the following:

Three new heteropentacene derivatives I (4–6; R¹ = R² = Me; R¹ = R² = C₆H₁₃; R¹ = Me, R² = H) based on bis(benzothieno)silole were synthesized. The XRD characterization reveals that the crystal structures of the heteropentacenes can be significantly influenced by the Me substitution. The optical and electrochem. properties were investigated and the exptl. results confirm that the silole motif lowers the LUMO level of the heteropentacenes. Preliminary results show that the insertion of silole ring systems into rigid heteropentacenes leads to an improved solubility and high fluorescence quantum yield up to 0.74 in solution, which indicates the potential of these new silole-containing compounds for photonic and photoelec. applications. The strong and sensitive fluorescence quenching behavior towards picric acid (PA) demonstrates that the silole-containing heteropentacene derivatives are also promising fluorescent sensor materials for detecting the nitro-containing explosives. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Electric Literature of C8H4Br2S).

2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The electrophilic substitution of benzothiophene systems is much less regioselective than that of indoles. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.Electric Literature of C8H4Br2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis and properties of 1-(2-methyl-3-benzothiophene)-2-[2-methyl-5-(3-fluoro-4-chloro)phenyl-3-thienyl]perfluorocyclopentene was written by Liao, Guanming;Zheng, Chunhong;Pu, Shouzhi. And the article was included in Advanced Materials Research (Durnten-Zurich, Switzerland) in 2015.Category: benzothiophene This article mentions the following:

An asym. photochromic diarylethene 1-(2-methyl-3-benzothiophene)-2-[2-methyl-5-(3-fluoro-4-chlorophenyl)-3-thienyl]perfluorocyclopentene (I) was synthesized and its photochromic, fluorescent properties were investigated in detail. This compound exhibited remarkable photochromism, upon irradiation with 297 nm UV light, the colorless solution of I turned to violet red with a new visible absorption band centered at 538 nm (ε = 1.17 Χ 10⁴ L mol^-1 cm^-1) attributable to the closed-ring isomer. The kinetic experiments showed that the cyclization and cycloreversion processes were zeroth and first order reaction, resp. Moreover, diarylethene I also exhibited obviously fluorescence switches along with the photochromism. The emission intensity of diarylethene I in a photostationary state was quenched to ca. 27% in hexane. In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9Category: benzothiophene).

3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9) belongs to benzothiophene derivatives. Functionalized benzothiophenes are important constructs found in molecules with wide ranging biological activity and in organic materials. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Category: benzothiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Tuning the redox properties of photochromic diarylethenes by introducing electron-withdrawing substituents was written by Berberich, Martin;Wuerthner, Frank. And the article was included in Asian Journal of Organic Chemistry in 2013.Computed Properties of C9H7BrS This article mentions the following:

A series of seven photochromic diarylethenes (DAEs) with various electron-withdrawing substituents and their resp. closed-form isomers (DAE_C) was synthesized and the optical and redox properties of these photochromes were investigated by UV/visible absorption spectroscopy and cyclic voltammetry. Our comparative studies with these DAEs revealed that the absorption properties of the closed forms and the redox potentials of the open and closed isomers appreciably depend on the number and nature of the electron-withdrawing groups introduced into the DAE unit. The DAE derivatives can be photochem. switched between two different states with different redox properties. Most prominently, the photochrome with two nitro groups has a first reduction potential for the open form of -1.51 V and for the corresponding closed form of -0.96 V, and, therefore, is particularly interesting as switchable electron-acceptor moiety in photochromic systems. In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9Computed Properties of C9H7BrS).

3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The electrophilic substitution of benzothiophene systems is much less regioselective than that of indoles. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, sertaconazole, and also BTCP.Computed Properties of C9H7BrS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis of a novel family of photochromic amorphous molecular materials based on dithienylethene, their photochromic properties and application for dual image formation was written by Utsumi, Hisayuki;Nagahama, Daisuke;Nakano, Hideyuki;Shirota, Yasuhiko. And the article was included in Journal of Materials Chemistry in 2002.Safety of 3-Bromo-2-methylbenzo[b]thiophene This article mentions the following:

A novel family of photochromic amorphous mol. materials containing a dithienylethene moiety, 1-{5-[4-(di-p-tolylamino)phenyl]-2-methylthiophen-3-yl}-2-(2,5-dimethylthiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopentene, 1-{5-[4-(di-p-tolylamino)phenyl]-2-methylthiophen-3-yl}-2-(2-methylbenzo[b]thiophen-3-yl)-3,3,4,4,5,5-hexafluorocyclopentene and 1,2-bis{5-[4-(di-p-tolylamino)phenyl]-2-methylthiophen-3-yl}-3,3,4,4,5,5-hexafluorocyclopentene, have been designed and synthesized. These compounds, together with their photocyclized products, were found to readily form amorphous glasses with well-defined glass transition temperatures and to undergo photochromism as amorphous films as well as in solution These compounds are characterized by high quantum yields for the photocyclization reactions, very low quantum yields for the reverse ring-opening reactions and, hence, almost 100% fractions of the photocyclized form at the photostationary state in solution These results suggest that the anti-parallel conformer is more populated than the parallel conformer. Optical dichroism was induced by irradiation of colored films of the photocyclized compounds with linearly polarized red light, and dual image formation at the same location was realized by utilizing this phenomenon. In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9Safety of 3-Bromo-2-methylbenzo[b]thiophene).

3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9) belongs to benzothiophene derivatives. Benzothiophene is a fused ring compound of thiophene ring and benzene ring, which is an important class of heterocycles with advantageous structures. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, sertaconazole, and also BTCP.Safety of 3-Bromo-2-methylbenzo[b]thiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Transition-Metal-Free Synthesis of 1,2-Disubstituted Indoles was written by Chesnokov, Gleb A.;Ageshina, Alexandra A.;Topchiy, Maxim A.;Nechaev, Mikhail S.;Asachenko, Andrey F.. And the article was included in European Journal of Organic Chemistry in 2019.COA of Formula: C9H7BrS This article mentions the following:

A new transition-metal-free robust and cost-effective method for synthesis of 1,2-disubstituted indoles from easily available unactivated (i.e. without EWG, PPh₃ or SiR₃ groups) tertiary amides. Scope of synthetic applicability of the presented protocol was shown on 23 examples of 1,2-disubstituted indoles with different substitution patterns obtained in good to excellent yields. The reported method turned out to be especially effective for synthesis of N-arylated 2-CF₃-indoles. Moreover, this approach can be performed in a one-pot two-step manner directly from com. available secondary amines. Mechanistic studies showed that acyl transfer might be an important step in the course of the reaction. Viability of the presented approach for benzofurans and benzothiophenes synthesis was also discussed. In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9COA of Formula: C9H7BrS).

3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The core structure is a part of various pharmaceutical substances and natural products. It is found within the chemical structures of pharmaceutical drugs such as zileuton, raloxifene, and sertaconazole, and also BTCP.COA of Formula: C9H7BrS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

An efficient novel synthesis of β-(azuleno[1,2-b]benzothienyl)- and β-(azuleno[2,1-b]benzothienyl)-α,β-unsaturated ketones by the tropylium ion-mediated intramolecular furan ring-opening reaction and X-ray investigation of methyl ketone derivative was written by Yamamura, Kimiaki;Houda, Yuuko;Hashimoto, Masao;Kimura, Takatomo;Kamezawa, Makoto;Otani, Takehiko. And the article was included in Organic & Biomolecular Chemistry in 2004.Product Details of 6287-82-7 This article mentions the following:

Intramol. reaction of 2-tropylio-3-(5-substituted 2-furyl)benzothiophenes, prepared from the corresponding 2-cycloheptatrienyl-3-(5-substituted 2-furyl)benzothiophenes, afforded the β-(azuleno[1,2-b]benzothienyl)-α,β-unsaturated ketones, e.g., I, which are otherwise difficult to obtain, in moderate yields. The reaction involves a ring-opening process of the furan ring by intramol. attack of the tropylium ion onto the 2-position of the furan ring. Similarly, β-(azuleno[2,1-b]benzothienyl)-α,β-unsaturated ketones were obtained from the corresponding 3-tropylio-2-(5-substituted 2-furyl)benzothiophenes albeit in lower yields. The mol. and crystal structures of the Me ketone derivative, 8a, are discussed on the basis of X-ray structure anal. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Product Details of 6287-82-7).

2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7) belongs to benzothiophene derivatives. Benzothiophene finds use in research as a starting material for the synthesis of larger, usually bioactive structures. The different substitution patterns in these heterocycles offer new opportunities for drug discovery and other applications in materials science.Product Details of 6287-82-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Discovery of LSZ102, a Potent, Orally Bioavailable Selective Estrogen Receptor Degrader (SERD) for the Treatment of Estrogen Receptor Positive Breast Cancer was written by Tria, George S.;Abrams, Tinya;Baird, Jason;Burks, Heather E.;Firestone, Brant;Gaither, L. Alex;Hamann, Lawrence G.;He, Guo;Kirby, Christina A.;Kim, Sunkyu;Lombardo, Franco;Macchi, Kaitlin J.;McDonnell, Donald P.;Mishina, Yuji;Norris, John D.;Nunez, Jill;Springer, Clayton;Sun, Yingchuan;Thomsen, Noel M.;Wang, Chunrong;Wang, Jianling;Yu, Bing;Tiong-Yip, Choi-Lai;Peukert, Stefan. And the article was included in Journal of Medicinal Chemistry in 2018.Formula: C9H8OS This article mentions the following:

In breast cancer, estrogen receptor alpha (ERα) pos. cancer accounts for approx. 74% of all diagnoses, and in these settings, it is a primary driver of cell proliferation. Treatment of ERα pos. breast cancer has long relied on endocrine therapies such as selective estrogen receptor modulators, aromatase inhibitors, and selective estrogen receptor degraders (SERDs). The steroid-based anti-estrogen fulvestrant, the only approved SERD, is effective in patients who have not previously been treated with endocrine therapy as well as in patients who have progressed after receiving other endocrine therapies. Its efficacy, however, may be limited due to its poor physicochem. properties. THe authors describe the design and synthesis of a series of potent benzothiophene-containing compounds that exhibit oral bioavailability and preclin. activity as SERDs. This article culminates in the identification of LSZ102 (I), a compound in clin. development for the treatment of ERα pos. breast cancer. In the experiment, the researchers used many compounds, for example, 6-Methoxybenzo[b]thiophene (cas: 90560-10-4Formula: C9H8OS).

6-Methoxybenzo[b]thiophene (cas: 90560-10-4) belongs to benzothiophene derivatives. Benzothiophene is used as starting material for the synthesis of bioactive molecules. The core structure is a part of various pharmaceutical substances and natural products. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.Formula: C9H8OS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Diastereoselective self-assembly of a triple-stranded europium helicate with light modulated chiroptical properties was written by Zhang, Zhihui;Zhou, Yanyan;Gao, Ting;Yan, Pengfei;Zou, Xiaoyan;Li, Hongfeng. And the article was included in Dalton Transactions in 2021.Formula: C9H7BrS This article mentions the following:

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 and R- and S-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 by ¹H, ¹⁹F, ³¹P NMR and DOSY NMR analyses. Also, the mirror-image CD and CPL spectra also demonstrate the existence of stable ground- and excited-state chiralities in solution When exposed to alternate UV 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 and g_lum switches. With these light-modulated optical outputs, the possibility for the fabrication of IMPLICATION and INHIBIT logic gates is discussed. In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9Formula: C9H7BrS).

3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9) belongs to benzothiophene derivatives. Benzothiophene scaffolds are of great importance due to its increased presence in bioactive molecules. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Formula: C9H7BrS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem