Heterocyclic Building Blocks-Benzothiophene

In 2022,Paganelli, Stefano; Tassini, Riccardo; Piccolo, Oreste published an article in ChemistrySelect. The title of the article was 《Sustainable Synthesis of Aryl and Heteroaryl Aldehydes》.Recommanded Product: 1-Thiophen-2-yl-ethanone The author mentioned the following in the article:

In this paper, authors’ focused on the synthesis of some (hetero)aromatic aldehydes, used either as industrial flavor/fragrances of com. interest, such as heliotropine, or as key intermediates for the preparation of some APIs and of other fragrances such as lioral and helional, by reductive carbonylation of halo derivative precursors. In order to carry out an easier and more applicable process, hydrogen donors, instead of gaseous flammable and explosive hydrogen, and recyclable phosphine free low metal content catalysts, were employed. In the experiment, the researchers used 1-Thiophen-2-yl-ethanone(cas: 88-15-3Recommanded Product: 1-Thiophen-2-yl-ethanone)

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Specialized thiophenes can be synthesized similarly using Lawesson’s reagent as the sulfidizing agent, or via the Gewald reaction, which involves the condensation of two esters in the presence of elemental sulfur. Another method is the Volhard–Erdmann cyclization. Recommanded Product: 1-Thiophen-2-yl-ethanone

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

《Metalation of 3-thiophenecarboxaldehyde ethylene acetal-the tautomeric structure of 3-formyl-2-thiophenecarboxylic acid》 was published in Arkiv foer Kemi in 1963. These research results belong to Gronowitz, Salo; Gestblom, Bo; Mathiasson, Birgitta. Category: benzothiophene The article mentions the following:

Metalation of 3-thiophenecarboxaldehyde ethylene acetal, b10 103-4°, with BuLi, followed by carbonation gave 78% 3formyl-2-thiophenecarboxylic acid (I), m. 130-1° (C6H6-ligroine). I was identified by mutual coupling of the thiophenic ring hydrogens at 5.2 cycles/sec. in the nuclear magnetic resonance (n.m.r.) spectrum and Ag2O oxidation of I to 2,3-thiophenedicarboxylic acid. The infrared spectrum of I in KBr showed C:O stretching frequencies at 5.87 and 6.09 μ, and no OH stretching absorption at 3 μ. I gave no Me ester on refluxing with MeOH without acid, but with acid a Me ester (II), m. 61-2°; v 5.81, 5.96 μ (KBr). Thus, I must exist in the open aldehydocarboxylic acid structure. The n.m.r, spectra are given for I, II, phthalaldehydic acid (III), the Me ester of III, and the anion of III in Me2CO, dioxane, CHCl3, and H2O. These spectra support the open form of I and the cyclic nature of III. In addition to this study using 2-(Thiophen-3-yl)-1,3-dioxolane, there are many other studies that have used 2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3Category: benzothiophene) was used in this study.

2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3) is one of dioxolane. 1,3-Dioxolane derivatives are recognized as important motifs for the construction of numerous pharmacologically active molecules as antiviral, antifungal, anti-HIV, and adrenoreceptor antagonists.Category: benzothiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

《Thiophene isosters of isoquinoline. VI. Synthesis of 4,5-dimethylthieno[2,3-c]pyridine and 6,7-dimethylthieno[3,2-c]pyridine》 was published in Chemica Scripta in 1975. These research results belong to Sandberg, Elina. SDS of cas: 13250-82-3 The article mentions the following:

4,7-Dimethylthieno[2,3-c]pyridine (I) was synthesized by hydrolyzing the acetal function in 2-amino-3-[2-(1,3-dioxolan-2-yl)-3-thienyl]butan-3-ol (II) leading to the ring-closed and dehydrated product. The amine was obtained by the reaction of 2-(3-lithio-2-thienyl)-1,3-dioxolane with diacetyl, followed by oximation and reduction 6,7-Dimethylthieno[3,2-c]pyridine (III) was obtained in an analogous manner. The experimental part of the paper was very detailed, including the reaction process of 2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3SDS of cas: 13250-82-3)

2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3) is one of dioxolane. 1,3-Dioxolane derivatives are recognized as important motifs for the construction of numerous pharmacologically active molecules as antiviral, antifungal, anti-HIV, and adrenoreceptor antagonists.SDS of cas: 13250-82-3

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

In 1988,Chemica Scripta included an article by Gronowitz, Salo; Hoernfeldt, Anna Britta; Yang, Youhua. SDS of cas: 13250-82-3. The article was titled 《Synthesis of dithienopyridines through palladium(0)-catalyzed coupling of 2-tributylstannyl-2-thiophenecarboxaldehyde with t-butyl N-(ortho-halothienyl)carbamates》. The information in the text is summarized as follows:

The title aldehyde (I) reacted with N-(o-halothienyl)carbamate esters, such as carbamate II, and Pd(PPh3)4 to give dithienopyridines III (R1R2 = CH:CHS, SCH:CH) and IV. I, tert-Bu N-(3-iodo-2-thienyl)carbamate, and Pd(PPh3)4 gave III (R1R2 = SCH:CH). The results came from multiple reactions, including the reaction of 2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3SDS of cas: 13250-82-3)

2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3) is one of dioxolane. 1,3-Dioxolane derivatives are recognized as important motifs for the construction of numerous pharmacologically active molecules as antiviral, antifungal, anti-HIV, and adrenoreceptor antagonists.SDS of cas: 13250-82-3

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

The author of 《Benzodithiophenes. A general method of synthesis》 were Gronowitz, Salo; Dahlgren, Torsten. And the article was published in Chemica Scripta in 1977. Recommanded Product: 2-(Thiophen-3-yl)-1,3-dioxolane The author mentioned the following in the article:

Through the Wittig reaction between o-bromoformylthiophenes and o-bromothenyltriphenylphosphoranes all six cis-1,2-di(o-bromothienyl)ethenes could be obtained. Halogen-metal exchange of these compounds with BuLi followed by reaction with CuCl2 yielded all six benzodithiophenes which are analogous to phenanthrene, namely benzo[1,2-b:4,3-b’]dithiophene, benzo[2,1-b:3,4-b’]dithiophene, benzo[1,2-b:3,4-b’]dithiophene, benzo[1,2-b:3,4-c’]dithiophene, benzo[2,1-b:3,4-c’]dithiophene and benzo[1,2-c:3,4-c’]dithiophene. The [b,c]-fused systems, although relatively stable in solution, could not be isolated due to dimerization or polymerization They could be characterized by reaction with di-Me acetylenedicarboxylate. After S extrusion, 7,8-dicarbomethoxynaphtho[2,1-b]thiophene and 7,8-dicarbomethoxynaphtho[1,2-b]thiophene are formed from the corresponding cycloaddition products. The other four benzodithiophenes did not react in the Diels-Alder reaction. The results came from multiple reactions, including the reaction of 2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3Recommanded Product: 2-(Thiophen-3-yl)-1,3-dioxolane)

2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3) is one of dioxolane. 1,3-Dioxolane derivatives are recognized as important motifs for the construction of numerous pharmacologically active molecules as antiviral, antifungal, anti-HIV, and adrenoreceptor antagonists.Recommanded Product: 2-(Thiophen-3-yl)-1,3-dioxolane

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

In 2019,Current Organic Synthesis included an article by Su, Biyun; Li, Yaning; Pan, Dandan; Faida, Paison; Yan, Tingyu; Qu, Zhan. Quality Control of 1-Thiophen-2-yl-ethanone. The article was titled 《Microwave Irradiation Syntheses and Crystal Structures of Two Series of Novel Fivemembered Heterocyclic Mono-Imine Compounds》. The information in the text is summarized as follows:

In order to increase the coordination ability of heteroatom N and S to center metals, CH3 group was introduced into the side arm of pyrrole imine and thiophene imine resp., to get two series of novel five-membered heterocyclic imine compounds, mono(imino)pyrroles and mono(imino)thiophenes. Two series of novel five-membered heterocyclic compounds with the mono-imine group were synthesized from the p-toluene sulfonic acid catalyzed Schiff base condensation of anilines and 2-acetylpyrrole/ 2-acetylthiophene resp., using CH3 group to substitute the common H atom on the side arm of pyrrole imine/ thiophene imine. All the heterocyclic mono-imine compounds were characterized adequately by means of 1H NMR, 13C NMR, FT-IR, elementary anal., as well as X-ray crystallog. diffraction. The reactivity differences between two precursor 2-acetylpyrrole and 2-acetylthiophene with aromatic amines were compared and discussed in detail. Compared to traditional heating methods, the solvent-free microwave irradiation seemed more efficient to prepare these series of five-membered heterocyclic mono-imine compounds, which resulted in a higher yield and cleaner product. In addition to this study using 1-Thiophen-2-yl-ethanone, there are many other studies that have used 1-Thiophen-2-yl-ethanone(cas: 88-15-3Quality Control of 1-Thiophen-2-yl-ethanone) was used in this study.

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Specialized thiophenes can be synthesized similarly using Lawesson’s reagent as the sulfidizing agent, or via the Gewald reaction, which involves the condensation of two esters in the presence of elemental sulfur. Another method is the Volhard–Erdmann cyclization. Quality Control of 1-Thiophen-2-yl-ethanone

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

The author of 《PTSA-Catalyzed Reaction of Alkyl/Aryl Methyl Ketones with Aliphatic Alcohols in the Presence of Selenium Dioxide: A Protocol for the Generation of an α-Ketoacetals Library》 were Shangpliang, O. Risuklang; Wanniang, Kmendashisha; Kshiar, Baskhemlang; Marpna, Ibakyntiew D.; Lipon, Tyrchain Mitre; Mizar, Pushpak; Myrboh, Bekington. And the article was published in ACS Omega in 2019. Application of 88-15-3 The author mentioned the following in the article:

A novel approach has been developed for the synthesis of a wide range of α-ketoacetals by the reaction of alkyl/aryl Me ketones and aliphatic alcs. in presence of selenium dioxide catalyzed by p-toluenesulfonic acid (PTSA). This method represents a general route to obtain a wide variety of α-ketoacetals in a simple, rapid and practical manner. This approach is particularly attractive because of the easily availability of the starting materials, mild reaction temperature and good yields of the products. The resulting α-ketoacetals are of much synthetic value as organic intermediates. In addition to this study using 1-Thiophen-2-yl-ethanone, there are many other studies that have used 1-Thiophen-2-yl-ethanone(cas: 88-15-3Application of 88-15-3) was used in this study.

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Reflecting their high stabilities, thiophenes arise from many reactions involving sulfur sources and hydrocarbons, especially unsaturated ones. Thiophenes are classically prepared by the reaction of 1,4-diketones, diesters, or dicarboxylates with sulfidizing reagents such as P4S10 such as in the Paal-Knorr thiophene synthesis. Application of 88-15-3

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

《Direct synthesis of secondary amides from ketones through Beckmann rearrangement using O-(mesitylsulfonyl)hydroxylamine》 was written by Chandra, Dinesh; Verma, Saumya; Pandey, Chandra Bhan; Yadav, Ajay K.; Kumar, Puneet; Tiwari, Bhoopendra; Jat, Jawahar L.. Safety of 1-Thiophen-2-yl-ethanone And the article was included in Tetrahedron Letters in 2020. The article conveys some information:

A highly efficient direct method for the preparation of secondary amides and lactams from ketones using O-(mesitylsulfonyl)hydroxylamine (MSH) was developed. The reactions proceeded rapidly at room temperature under mild condition without requiring any additive and tolerate multiple functional groups. A simple aqueous work-up often furnished the products in excellent yield with high purity. In addition to this study using 1-Thiophen-2-yl-ethanone, there are many other studies that have used 1-Thiophen-2-yl-ethanone(cas: 88-15-3Safety of 1-Thiophen-2-yl-ethanone) was used in this study.

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Reflecting their high stabilities, thiophenes arise from many reactions involving sulfur sources and hydrocarbons, especially unsaturated ones. Thiophenes are classically prepared by the reaction of 1,4-diketones, diesters, or dicarboxylates with sulfidizing reagents such as P4S10 such as in the Paal-Knorr thiophene synthesis. Safety of 1-Thiophen-2-yl-ethanone

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Kuzu, Burak; Ekmekci, Zeynep; Tan, Meltem; Menges, Nurettin published an article in 2021. The article was titled 《Excited State Intramolecular Proton Transfer (ESIPT)-Based Sensor for Ion Detection》, and you may find the article in Journal of Fluorescence.COA of Formula: C6H6OS The information in the text is summarized as follows:

C-2 and C-5 substituted imidazole skeleton was synthesized through a one-pot two-step strategy. Synthesized mol. emits the light on ESIPT (excited-state intramol. proton transfer). This mol. was utilized for its proton donor ability, and we have observed that fluoride and cyanide ions can be detected selectively. Different cations and anions were selected to observe the response of the synthesized mol. However, there were not any fluorometric and colorimetric response except for fluoride and cyanide ions. Detection limits of fluoride and cyanide ions were found to be 9.22μM and 11.48μM, resp. 1H-NMR spectra for the solution of the sensor and TBAF (tetrabuthylammoniumfluoride) were used for the identification of [L]-[HF2]- species. 3 equivalent TBAF saturated the solution of the sensor in d6-DMSO, and some of the proton resonances shifted to upfield due to the through-bond effect. The disappearance of NH proton with 0.5 equivalent TBAF or TBACN (tetrabuthylammoniumcyanide) showed that there was a proton abstraction by fluoride and cyanide ions, instead of the hydrogen bond. Solid-state application was utilized, and paper test strips were applied. Emission differences emerged when the sensor loaded strips were reacted with TBAF. Time resolved experiments revealed that solution of the sensor and TBAF in DMSO have multiexponential decay, and one of the lifetime was measured as 13.4 ns. In addition to this study using 1-Thiophen-2-yl-ethanone, there are many other studies that have used 1-Thiophen-2-yl-ethanone(cas: 88-15-3COA of Formula: C6H6OS) was used in this study.

1-Thiophen-2-yl-ethanone(cas: 88-15-3) belongs to thiophenes. Specialized thiophenes can be synthesized similarly using Lawesson’s reagent as the sulfidizing agent, or via the Gewald reaction, which involves the condensation of two esters in the presence of elemental sulfur. Another method is the Volhard–Erdmann cyclization. COA of Formula: C6H6OS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Li, Chung-Yen; Su, Chaochin; Wang, Hsiou-Hsuan; Kumaresan, Prabakaran; Hsu, Chia-Hsuan; Lee, I.-Ting; Chang, Wei-Chun; Tingare, Yogesh S.; Li, Ting-Yu; Lin, Chia-Feng; Li, Wen-Ren published an article on January 31 ,2014. The article was titled 《Design and development of cyclometalated ruthenium complexes containing thiophenyl-pyridine ligand for dye-sensitized solar cells》, and you may find the article in Dyes and Pigments.SDS of cas: 220180-55-2 The information in the text is summarized as follows:

Two new cyclometalated Ru sensitizers NC102(1) and NC103(2), where the 2 NCS- ligands of the N3 analog were replaced with the 2-thiophen-2-yl-pyridine and 2-benzo[b]thiophen-2-yl-pyridine ligands, resp., were designed and synthesized for dye-sensitized solar cell applications. The effects of these 2 ligands on the photophys. behavior of Ru complexes were studied by their optical, electrochem., and photovoltaic properties. The sensitizer NC103(2) with the fluoride substitution in the ligand exhibited the best cell performance with a short-circuit current (Jsc) of 9.45 mA/cm2, an open-circuit voltage (Voc) of 630 mV, and a fill factor (FF) of 0.71, giving an overall power conversion efficiency of (η) 4.22% under simulated AM 1.5 irradiation In addition to this study using Methyl 4-fluorobenzo[b]thiophene-2-carboxylate, there are many other studies that have used Methyl 4-fluorobenzo[b]thiophene-2-carboxylate(cas: 220180-55-2SDS of cas: 220180-55-2) was used in this study.

Methyl 4-fluorobenzo[b]thiophene-2-carboxylate(cas: 220180-55-2) belongs to benzothiophene.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 selective estrogen receptor modulators, leukotriene synthesis inhibitors and antifungals, as well as in many natural products. SDS of cas: 220180-55-2

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem