Heterocyclic Building Blocks-Benzothiophene

Palladium-Catalyzed Direct Decarbonylative Cyanation of Aryl Carboxylic Acids was written by Zhang, Guofu;Miao, Huihui;Guan, Chenfei;Ding, Chengrong. And the article was included in Journal of Organic Chemistry in 2022.COA of Formula: C9H5NS This article mentions the following:

The direct transformation of aryl carboxylic acids to aryl nitrile compounds is an interesting topic because carboxylic acids are not only abundant in nature but are also inexpensive and stable. Here, the synthesis of a series of aryl nitriles by palladium-catalyzed decarbonylative cyanation of carboxylic acids without base has been achieved. The successful decarbonylative cyanation of drug mols. and gram-scale reaction to verify the practicality and operability of this method are analyzed. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9COA of Formula: C9H5NS).

Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9) 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.COA of Formula: C9H5NS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Iridium-Catalyzed Hydrogen Transfer: Synthesis of Substituted Benzofurans, Benzothiophenes, and Indoles from Benzyl Alcohols was written by Anxionnat, Bruno;Gomez Pardo, Domingo;Ricci, Gino;Rossen, Kai;Cossy, Janine. And the article was included in Organic Letters in 2013.Category: benzothiophene This article mentions the following:

An iridium-catalyzed hydrogen transfer has been developed in the presence of p-benzoquinone, allowing the synthesis of a diversity of substituted benzofurans, benzothiophenes, and indoles from substituted benzylic alcs. E.g., in presence of [IrCp^*Cl₂]₂, p-benzoquinone, and Cs₂CO₃, hydrogen transfer/cyclization of benzylic alc. (I) gave 98% benzofuran derivative (II). In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9Category: benzothiophene).

Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9) belongs to benzothiophene derivatives. Benzothiophene scaffolds are of great importance due to its increased presence in bioactive molecules. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, and sertaconazole, and also BTCP.Category: benzothiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Dually Switchable Heterotetracenes: Addressing the Photophysical Properties and Self-Organization of the P-S System was written by Ren, Yi;Baumgartner, Thomas. And the article was included in Journal of the American Chemical Society in 2011.Related Products of 6287-82-7 This article mentions the following:

New ladder-type, phosphorus- and sulfur-based heterotetracenes were synthesized, which allowed the engineering of the materials’ properties by exploitation of the different reactivities between sulfur and phosphorus. ³¹P NMR spectroscopy and x-ray crystallog. studies revealed that the different electronic effects of the secondary heteroatom, sulfur, influence not only the conjugation in the heterotetracene core but also the behavior of the phosphorus center. UV-vis and fluorescence spectroscopy showed that the scaffold’s band gap is mainly controlled by the electronic nature of sulfur, while the fluorescence quantum yield highly depends on the electronic nature of phosphorus. Cyclic voltammetry indicated that the redox properties of the system could be altered by selective modification of the resp. heteroatom (oxidation of sulfur and/or functionalization of trivalent phosphorus). Importantly, oxidation of the phosphorus center results in enhanced reduction features of the heterotetracene system, and oxidation of the sulfur center further enhances the electron acceptor character of the core. Theor. calculations provided insights on both selectivity of phosphorus chem. and communication between the two heteroatoms (sulfur and phosphorus). Macroscopic self-organization of the heterotetracenes was observed when the tetracene core is functionalized with pendant functional groups. Preliminary results showed that extension of the mol. with an alkyl chain along the long axis of mols. induces the formation of 1D microfibers, which was confirmed by fluorescence microscopy and SEM. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Related Products of 6287-82-7).

2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7) belongs to benzothiophene derivatives. Benzothiophenes are valuable heterocycles that are widely used in medicines, agrochemicals, and materials science. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.Related Products of 6287-82-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Photochromism and fluorescence of a novel unsymmetrical diarylethene material bearing benzene and thiophene ring was written by Jing, Shuhong;Pu, Shouzhi;Li, Hui. And the article was included in Applied Mechanics and Materials in 2012.SDS of cas: 10243-15-9 This article mentions the following:

A new photochromic diarylethene compound, 1-[2-methyl-(5-(4- dioxolane) phenyl)-3-thienyl]-2-(2-methyl-3-benzothiophene)perfluorocyclopentene (1o) was synthesized. Its properties, including photochromism and fluorescence were investigated in detail both in solution and PMMA amorphous film. It underwent reversible cyclization and cycloreversion reactions upon alternating irradiation with UV and visible light in hexane. The compound showed good photochromism both in solution and in solid states. Diarylethene 1o changed the color from colorless to purple upon irradiation with 297 nm UV light, in which absorption maxima were observed at 539 nm in hexane and at 547 nm in PMMA film, resp. Using diarylethene 1c/PMMA film as recording medium, optical recording was performed successfully. This new photochromic system also exhibited remarkable optical storage character. In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9SDS of cas: 10243-15-9).

3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9) belongs to benzothiophene derivatives. Benzothiophene finds use in research as a starting material for the synthesis of larger, usually bioactive 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.SDS of cas: 10243-15-9

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Palladium-catalyzed tandem N-H/C-H arylation: regioselective synthesis of N-heterocycle-fused phenanthridines as versatile blue-emitting luminophores was written by Yan, Lipeng;Zhao, Dongbing;Lan, Jingbo;Cheng, Yangyang;Guo, Qiang;Li, Xiaoyu;Wu, Ningjie;You, Jingsong. And the article was included in Organic & Biomolecular Chemistry in 2013.Category: benzothiophene This article mentions the following:

A general and highly regioselective synthetic protocol for structurally diverse N-heteroaryl-fused phenanthridines has been developed. Varieties of fluorescence mols. comprising imidazole-fused, benzoimidazole-fused, indole-fused and pyrrole-fused phenanthridines were obtained by this modular approach, some of which exhibit excellent blue-emitting performance, high quantum yields, long fluorescence lifetimes, interesting electrochem. properties, and thermal stabilities. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Category: benzothiophene).

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. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Category: benzothiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Photoredox Catalysis Enables Access to N-Functionalized 2,1-Borazaronaphthalenes was written by Wang, Xie;Davies, Geraint H. M.;Koschitzky, Adriel;Wisniewski, Steven R.;Kelly, Christopher B.;Molander, Gary A.. And the article was included in Organic Letters in 2019.Application In Synthesis of Methyl 5-bromobenzo[b]thiophene-2-carboxylate This article mentions the following:

The synthesis and use of a class of 2,1-borazaronaphthyltrifluoroborate reagents that provide a general solution to the challenge of N-functionalization of the 2,1-borazaronaphthalene core is described. By adorning the N of this core with a trifluoroboratomethyl unit, a suite of odd-electron processes can be executed, installing motifs that would otherwise be inaccessible using a two-electron approach. This process enables rapid annulation, furnishing a heretofore unknown polycyclic B-N species. In the experiment, the researchers used many compounds, for example, Methyl 5-bromobenzo[b]thiophene-2-carboxylate (cas: 7312-11-0Application In Synthesis of Methyl 5-bromobenzo[b]thiophene-2-carboxylate).

Methyl 5-bromobenzo[b]thiophene-2-carboxylate (cas: 7312-11-0) 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.Application In Synthesis of Methyl 5-bromobenzo[b]thiophene-2-carboxylate

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Copper-mediated cyanation of aryl boronic acids using benzyl cyanide was written by Luo, Yan;Wen, Qiaodong;Wu, Zhiyuan;Jin, Jisong;Lu, Ping;Wang, Yanguang. And the article was included in Tetrahedron in 2013.Computed Properties of C9H5NS This article mentions the following:

An efficient copper-mediated synthesis of aryl nitriles from arylboronic acids was achieved using benzyl cyanide as a user-friendly cyanide source. Various arylboronic acids underwent the reaction smoothly, affording the corresponding aryl nitriles in moderate to good yields. Tert-Bu hydroperoxide (TBHP) was found to be a critical agent facilitating the cyanation. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9Computed Properties of C9H5NS).

Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9) belongs to benzothiophene derivatives. Benzothiophene finds use in research as a starting material for the synthesis of larger, usually bioactive structures. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.Computed Properties of C9H5NS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Transformation of aromatic bromides into aromatic nitriles with n-BuLi, pivalonitrile and iodine under metal cyanide-free conditions was written by Uchida, Ko;Togo, Hideo. And the article was included in Tetrahedron in 2019.HPLC of Formula: 55219-11-9 This article mentions the following:

Various aromatic nitriles ArCN [Ar = Ph, 4-BrC₆H₄, 5-ethyl-2-furyl, etc.] were obtained in good yields by the treatment of aryl bromides with n-butyllithium and then pivalonitrile, followed by the treatment with mol. iodine at 70 °C, without metal cyanides under transition-metal-free conditions. The present reaction proceeded through the radical β-elimination of imino-nitrogen-centered radicals formed from the reactions of imines and N-iodoimines under warming conditions. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9HPLC of Formula: 55219-11-9).

Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9) belongs to benzothiophene derivatives. Benzothiophene scaffolds are of great importance due to its increased presence in bioactive molecules. It is found within the chemical structures of pharmaceutical drugs such as zileuton, raloxifene, and sertaconazole, and also BTCP.HPLC of Formula: 55219-11-9

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Self-Contained Photoacid Generator Triggered by Photocyclization of Triangle Terarylene Backbone was written by Nakashima, Takuya;Tsuchie, Kenta;Kanazawa, Rui;Li, Ruiji;Iijima, Shunsuke;Galangau, Olivier;Nakagawa, Hisako;Mutoh, Katsuya;Kobayashi, Yoichi;Abe, Jiro;Kawai, Tsuyoshi. And the article was included in Journal of the American Chemical Society in 2015.HPLC of Formula: 6287-82-7 This article mentions the following:

We herein propose a new type of efficient neutral photoacid generator. A photoinduced 6π-electrocyclization reaction of photochromic triangle terarylenes triggers subsequent release of a Bronsted acid, which took place from the photocyclized form. A H-atom and its conjugate base were introduced at both sides of a 6π-system to form the self-contained photoacid generator. UV irradiation to the 6π-system produces a cyclohexa-1,3-diene part with a H-atom and a conjugate base on the sp³ C-atoms at 5- and 6-positions, resp., which spontaneously release an acid mol. quant. forming a polyaromatic compound A net quantum yield of photoacid generation as high as 0.52 under ambient conditions and a photoinitiated cationic polymerization of an epoxy monomer are demonstrated. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7HPLC of Formula: 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. It is also used in the manufacturing of dyes such as thioindigo.HPLC of Formula: 6287-82-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Reversible Photochemical Switching via Plasmonically Enhanced Upconversion Photoluminescence was written by Kim, Byunghoon;Lee, Kyu-Tae;Cho, Junhee;Darshanoju, Narasimha Achary;Jung, Kinam;Ahn, In-Hwan;Shin, Jae-Min;Oh, Hyeongyeol;Ki, Yeongcheol;Lee, Hohjai;Kwon, Seok Joon;Kim, In Soo;Cai, Wenshan;Ahn, Kwang-Hyun;Ko, Doo-Hyun. And the article was included in Advanced Optical Materials in 2021.Related Products of 10243-15-9 This article mentions the following:

Photochromic mol.-incorporated optical devices offer desirable properties for photocontrollable optical systems, including advanced optical data storage and super-resolution imaging. However, these mols. require multiple illumination sources, such as UV and visible light, for reversible photochem. reactions, which restricts their potential for advanced application. This study reports an effective strategy for modulating photoisomerization via a single near-IR light source assisted by plasmonically enhanced photoswitchable upconversion photoluminescence (UCPL). The proposed quasi-periodic metal nanostructures to facilitate the resonance modes in the broadband region enable the substitution of the detrimental high-energy light source (i.e., UV light) with near-IR stimuli, which is associated with UCPL enhancement of over two orders with spectrum orthogonality. To validate this concept, the accelerated reversible-photoisomerization kinetics is exptl. confirmed by three- and tenfold amplification of the PL intensities of the photochromic disulfonyldiarylethene derivatives Further validation of the proposed strategy is performed using photodynamic imaging, which reveals accelerated photoisomerization, high photocyclization stability, and high spatial resolution In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9Related Products of 10243-15-9).

3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9) belongs to benzothiophene derivatives. Benzothiophenes are valuable heterocycles that are widely used in medicines, agrochemicals, and materials science. It is found within the chemical structures of pharmaceutical drugs such as zileuton, raloxifene, and sertaconazole, and also BTCP.Related Products of 10243-15-9

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem