Category: benzothiophene

C-H arylation and alkenylation of imidazoles by nickel catalysis: solvent-accelerated imidazole C-H activation was written by Muto, Kei;Hatakeyama, Taito;Yamaguchi, Junichiro;Itami, Kenichiro. And the article was included in Chemical Science in 2015.Related Products of 6287-82-7 This article mentions the following:

The first nickel-catalyzed C-H arylations and alkenylations of imidazoles with phenol and enol derivatives are described. Under the influence of Ni(OTf)₂/dcype/K₃PO₄ (dcype: 1,2-bis(dicyclohexylphosphino)ethane) in t-amyl alc., imidazoles can undergo C-H arylation with phenol derivatives The C-H arylation of imidazoles with chloroarenes as well as that of thiazoles and oxazoles with phenol derivatives can also be achieved with this catalytic system. By changing the ligand to dcypt (3,4-bis(dicyclohexylphosphino)thiophene), enol derivatives could also be employed as coupling partners achieving the C-H alkenylation of imidazoles as well as thiazoles and oxazoles. Thus, a range of C2-arylated and alkenylated azoles can be synthesized using this newly developed nickel-based catalytic system. The key to the success of the C-H coupling of imidazoles is the use of a tertiary alc. as solvent. This also allows the use of an air-stable nickel(II) salt as the catalyst precursor. 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. Functionalized benzothiophenes are important constructs found in molecules with wide ranging biological activity and in organic materials. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, sertaconazole, and also BTCP.Related Products of 6287-82-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Photokinetics of two novel photochromic diarylethenes derived from benzothiophene was written by Vazquez, A.;Nudelman, N. Sbarbati. And the article was included in International Journal of Chemical Kinetics in 2012.SDS of cas: 90560-10-4 This article mentions the following:

Two new unsym. substituted photochromic diarylethenes, namely 3-[3, 3,4,4,5,5-hexafluoro-2-(2-methylbenzothien-3-yl)cyclopent-1-en-1-yl]-2-methyl-6-methoxy-1- benzothiophene and 3-[3,3,4,4,5,5-hexafluoro-2-(2-methylbenzothien-3-yl)cyclopent-1-en-1-yl]-2-methyl-6-methoxy-7-nitro-1-benzothiophene, were synthesized. Their optical properties and kinetics of cyclization and cycloreversion were determined in four solvents and compared with the sym. diarylethene (3,3,4,4,5,5-hexafluorocyclopent-1-en-1,2-diyl)bis(2-methyl-1-benzothiophene). While the UV spectra of the three compounds are almost insensitive to solvent changes, the rates of the ring-opening and ring-closure reactions exhibit interesting kinetic behavior that differs from other diarylethenes reported in the literature. The cycloreversion for the three compounds follows first-order kinetics, whereas the cyclization cannot be described by a simple kinetic law. Different approaches were tested, and a complex exponential equation could be derived that fits the exptl. data. The unusual presence of two ring-opened conformational isomers, one of them nonphotochromic, is proposed for the ring-opened compounds to explain the derived kinetic law and observed solvent effects. These results are of interest in relation to the application of the novel diarylethenes as potential optical materials. © 2012 Wiley Periodicals, Inc. Int J Chem Kinet 1-9, 2012. In the experiment, the researchers used many compounds, for example, 6-Methoxybenzo[b]thiophene (cas: 90560-10-4SDS of cas: 90560-10-4).

6-Methoxybenzo[b]thiophene (cas: 90560-10-4) belongs to benzothiophene derivatives. Benzothiophene finds use in research as a starting material for the synthesis of larger, usually bioactive structures. It is found within the chemical structures of pharmaceutical drugs such as zileuton, raloxifene, and sertaconazole, and also BTCP.SDS of cas: 90560-10-4

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

A convenient synthesis of 3,4-diaryl(hetaryl)-substituted maleimides and maleic anhydrides was written by Shorunov, S. V.;Krayushkin, M. M.;Stoyanovich, F. M.;Irie, M.. And the article was included in Russian Journal of Organic Chemistry in 2006.Synthetic Route of C9H7BrS This article mentions the following:

A convenient procedure has been developed for the synthesis of 3,4-diaryl(or hetaryl)maleimides by cross coupling of N-substituted 3,4-dibromomaleimides with aryl(hetaryl)boronic acids in the presence of Pd(Ph₃P)₄ and CsF. The reaction ensures high yields of the products and requires relatively small amount of the catalyst; it can be performed on an enlarged scale. The resulting maleimides are readily converted into the corresponding maleic anhydrides. 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 finds use in research as a starting material for the synthesis of larger, usually bioactive structures. It is found within the chemical structures of pharmaceutical drugs such as zileuton, raloxifene, and sertaconazole, and also BTCP.Synthetic Route of C9H7BrS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Reactions of bromothianaphthenes with piperidine. Reinvestigation was written by Reinecke, Manfred G.;Mohr, William B.;Adickes, H. Wayne;De Bie, D. A.;Van der Plas, H. C.;Nijdam, K.. And the article was included in Journal of Organic Chemistry in 1973.Safety of 2,3-Dibromobenzo[b]thiophene This article mentions the following:

The reaction of 3-bromothianaphthene with piperidine was reinvestigated and found to give primarily the normal (I) but also some of the cine-substitution product (II), which is also the only product from the reaction of 2-bromothianapthene. The previously reported results can be rationalized by the effects of air metals, and impure starting material on the reaction. 2,3-Dibromothianaphthene (III) also gives II under these conditions probably via the 2-piperidino-3-bromo analog (IV), which was isolated under milder conditions, could be converted to II in high yield, and was synthesized from II via an iminium salt. 2,3-Dipiperidinothianaphthene was isolated in trace amounts from the reactions of III and IV with piperidine. Possible mechanisms for some of these reactions are discussed. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Safety of 2,3-Dibromobenzo[b]thiophene).

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.Safety of 2,3-Dibromobenzo[b]thiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis of nitriles via the iodine-mediated dehydrosulfurization of thioamides was written by Murata, Yuki;Iwasa, Hitomi;Matsumura, Mio;Yasuike, Shuji. And the article was included in Chemical & Pharmaceutical Bulletin in 2020.SDS of cas: 55219-11-9 This article mentions the following:

A simple general method for the synthesis of nitriles using the inexpensive and easy to handle iodine (I₂) is described herein. The reaction of thioamides with I₂ in the presence of triethylamine at room temperature under aerobic conditions afforded various nitriles bearing aryl, vinyl, and alkyl groups in good-to-excellent yields. This method was also effective for conversion of thioureas to cyanamides. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9SDS of cas: 55219-11-9).

Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9) belongs to benzothiophene derivatives. Functionalized benzothiophenes are important constructs found in molecules with wide ranging biological activity and in organic materials. It is found within the chemical structures of pharmaceutical drugs such as zileuton, raloxifene, and sertaconazole, and also BTCP.SDS of cas: 55219-11-9

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Polymerization of a Photochromic Diarylethene by Friedel-Crafts Alkylation was written by Jeong, Yong-Chul;Park, Dae Gyu;Kim, Eunkyoung;Yang, Sung Ik;Ahn, Kwang-Hyun. And the article was included in Macromolecules in 2006.Safety of 3-Bromo-2-methylbenzo[b]thiophene This article mentions the following:

A high-d. diarylethene main-chain homopolymer, poly-BTF6, from the reaction of BTF6 with TiCl₄ and chloromethyl Me ether was synthesized and characterized. The new polymerization method is efficient to produce the polymers of various mol. weights in high yield. The polymer exhibits the characteristic photochromic property as the corresponding monomeric unit in solution and also in solid film. The fatigue resistance of the polymer to UV light was significantly improved compared with its monomer unit. This novel polymerization of a photochromic diarylethene using Friedel-Crafts alkylation could be widely applied in the polymerization of many functional aromatic compound as evidently shown by the dimerization of a benzothiopene derivative 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 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.Safety of 3-Bromo-2-methylbenzo[b]thiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Photochemical Transformation of O-(β-Arylethyl) Arylimidates into 2,4-Diaryl-5-iodoxazoles with 1,3-Diiodo-5,5-dimethylhydantoin was written by Saito, Aya;Togo, Hideo. And the article was included in European Journal of Organic Chemistry in 2020.Name: Benzo[b]thiophene-2-carbonitrile This article mentions the following:

Treatment of O-(β-arylethyl) arylimidates with 1,3-diiodo-5,5-dimethylhydantoin (DIH) under irradiation with a tungsten lamp in 1,2-dichloroethane gave the corresponding 2,4-diaryl-5-iodoxazoles and 2,4-diaryloxazoles in good to moderate yields, resp., depending on the aryl group. It is proposed that the reactions proceeded through the formation of N-iodoimidates by the reaction of O-(β-arylethyl) arylimidates with DIH, followed by the formation of iminyl radicals via homolytic N-I bond cleavage, the 1,5-H shift by the iminyl radicals, the C-I bond formation of the formed carbon-centered radicals with iodine, the nucleophilic cyclization by the imino groups to form 2,4-diaryloxazolines, the oxidation of the formed 2,4-diaryloxazolines to 2,4-diaryloxazoles, and the iodination of the formed 2,4-diaryloxazoles to 2,4-diaryl-5-iodoxazoles with DIH. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9Name: Benzo[b]thiophene-2-carbonitrile).

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. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.Name: Benzo[b]thiophene-2-carbonitrile

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Hydrotreating of halobenzo[b]thiophenes and their S-oxide and S,S-dioxide derivatives over cobalt(II) oxide-molybdenum(VI) oxide/alumina catalyst was written by Bonnet, M.;Geneste, P.;Guida, A.;Mampouya, D.. And the article was included in Journal of Catalysis in 1983.Name: 2,3-Dibromobenzo[b]thiophene This article mentions the following:

The title reaction was examined under stirred batch reactor conditions. The dehalogenation of the halobenzo[b]thiophenes (I) occurs without any hydrogenation or hydrodesulfurization. For the S-oxides deoxygenation occurs first; for the S,S-dioxides dehalogenation is the first step of the reaction. The LFER of the dehalogenation rate vs. the ionization potential of I shows that electronic effects are important in these reactions. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Name: 2,3-Dibromobenzo[b]thiophene).

2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7) belongs to benzothiophene derivatives. Benzothiophene scaffolds are of great importance due to its increased presence in bioactive molecules. The different substitution patterns in these heterocycles offer new opportunities for drug discovery and other applications in materials science.Name: 2,3-Dibromobenzo[b]thiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

One-pot conversion of aromatic bromides and aromatics into aromatic nitriles via aryllithiums and their DMF adduct was written by Ushijima, Sousuke;Moriyama, Katsuhiko;Togo, Hideo. And the article was included in Tetrahedron in 2011.HPLC of Formula: 55219-11-9 This article mentions the following:

Various aromatic bromides and iodides were smoothly converted into the corresponding aromatic nitriles in good to moderate yields by the treatment with n-butyllithium and subsequently DMF, followed by treatment with mol. iodine in aq NH₃. The same treatment of typical aromatics and heteroaromatics with n-butyllithium and subsequently DMF, followed by treatment with mol. iodine in aq NH₃ also provided the corresponding aromatic nitriles in good yields. Moreover, the same treatment of aromatic bromides and aromatics with half amount of DIH (1,3-diiodo-5,5-dimethylhydantoin) instead of mol. iodine worked effectively to give the corresponding aromatic nitriles, resp., in good yields. These reactions are novel and environmentally benign one-pot methods for the preparation of aromatic nitriles from aromatic bromides and aromatics, resp., through the formation of aryllithiums and their DMF adducts. 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 is relatively a stable molecule. The electrophilic substitution of benzothiophene systems is much less regioselective than that of indoles. The different substitution patterns in these heterocycles offer new opportunities for drug discovery and other applications in materials science.HPLC of Formula: 55219-11-9

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

C_17,20-Lyase inhibitors I. Structure-based de novo design and SAR study of C_17,20-lyase inhibitors was written by Matsunaga, Nobuyuki;Kaku, Tomohiro;Itoh, Fumio;Tanaka, Toshimasa;Hara, Takahito;Miki, Hiroshi;Iwasaki, Masahiko;Aono, Tetsuya;Yamaoka, Masuo;Kusaka, Masami;Tasaka, Akihiro. And the article was included in Bioorganic & Medicinal Chemistry in 2004.HPLC of Formula: 70060-13-8 This article mentions the following:

Novel nonsteroidal C_17,20-lyase inhibitors were synthesized using de novo design based on its substrate, 17α-hydroxypregnenolone, and several compounds exhibited potent C_17,20-lyase inhibition. However, in vivo activities in inhibiting testosterone biosynthesis were short-lasting, and to improve the duration of action, a series of benzothiophene derivatives were evaluated. As a result, 4-[(E)-4-(5-fluorobenzo[b]thiophen-2-yl)-3-buten-2-yl]-1H-imidazole, (S)-4-[(E)-4-(5-fluoro-3-methylbenzo[b]thiophen-2-yl)-3-buten-2-yl]-1H-imidazole, and 4-(E)-4-(5-fluorobenzo[b]thiophen-2-yl)-2-methyl-3-buten-2-yl-1H-imidazole (I) (IC₅₀=4-9 nM) and 4-[(E)-3-(5-fluoro-3-methylbenzo[b]thiophen-2-yl)-2-propen-1-yl]-1H-imidazole (IC₅₀=27 nM) were identified to have powerful in vivo efficacy with extended duration of action. The key structural determinants for the in vivo efficacy were demonstrated to be the 5-fluoro group on the benzothiophene ring and the 4-imidazolyl moiety. Superimposition of I and 17α-hydroxypregnenolone demonstrated their structural similarity and enabled rationalization of the pharmacol. results. In addition, selected compounds were also identified to be potent inhibitors of human enzyme with IC₅₀ values of 20-30 nM. These results suggest that some benzothiophene inhibitors described in this paper may be promising agents for the treatment of prostate cancer. In the experiment, the researchers used many compounds, for example, 5-Fluoro-1-benzothiophene-2-carboxylic acid (cas: 70060-13-8HPLC of Formula: 70060-13-8).

5-Fluoro-1-benzothiophene-2-carboxylic acid (cas: 70060-13-8) 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.HPLC of Formula: 70060-13-8

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem