Month: October 2022

HPLC of Formula: 88-15-3In 2022 ,《Determination of the semiexperimental equilibrium structure of 2-acetylthiophene in the presence of methyl internal rotation and substituent effects compared to thiophene》 was published in Physical Chemistry Chemical Physics. The article was written by Dindic, Christina; Ludovicy, Jil; Terzi, Vladimir; Luechow, Arne; Vogt, Natalja; Demaison, Jean; Nguyen, Ha Vinh Lam. The article contains the following contents:

The microwave spectra of thiophene and 2-acetylthiophene were recorded in the frequency range from 2 to 40 GHz using two mol. jet Fourier transform microwave spectrometers. For 2-acetylthiophene, two conformers with a syn and an anti orientation of the S1-C2 and C6=O bonds (with respect to the C2-C6 bond) were identified, and the syn-conformer was more stable. The spectra of the 34S- and 13C-isotopologues of syn-2-acetylthiophene were also assigned, and the semiexperimental equilibrium structure could be determined Compared to thiophene, at the substitution position, the S1-C2 and C2C3 bond lengths both increase by about 0.007 Å, and the bond angle S1-C2C3 decreases by 0.06°, noticeably larger than the exptl. uncertainties. A-E torsional splittings were observed due to internal rotation of the Me group hindered by a barrier height of 330.187(35) and 295.957(17) cm-1 for the syn-conformer and the anti-conformer, resp. Geometry and internal rotation parameters are compared with those of related thiophene derivatives, as well as those of furan and 2-acetylthiophene to gain a better understanding of structure determination in the presence of Me internal rotation. The results came from multiple reactions, including the reaction of 1-Thiophen-2-yl-ethanone(cas: 88-15-3HPLC of Formula: 88-15-3)

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. HPLC of Formula: 88-15-3

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

In 2019,Journal of Heterocyclic Chemistry included an article by Shelke, Premchand B.; Mali, Suraj N.; Chaudhari, Hemchandra K.; Pratap, Amit P.. Application In Synthesis of 1-Thiophen-2-yl-ethanone. The article was titled 《Chitosan hydrochloride mediated efficient, green catalysis for the synthesis of perimidine derivatives》. The information in the text is summarized as follows:

Chitosan hydrochloride as biopolymer-based, renewable and recyclable heterogeneous catalyst was used for efficient one-pot synthesis of 2,3-dihydro-1H-perimidine derivatives I [R1 = H, Me, Et, Ph; R2 = Me, Ph, 2-furyl, etc.; R1R2 = (CH2)5] via reaction of naphthalene-1,8-diamine with various ketones. This newly developed greener methodol. provided a very simple and greener route for the synthesis of perimidines in short time with excellent yield.1-Thiophen-2-yl-ethanone(cas: 88-15-3Application In Synthesis 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. Application In Synthesis of 1-Thiophen-2-yl-ethanone

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Formula: C6H6OSIn 2019 ,《Catalytic Enantioselective Addition of Prochiral Radicals to Vinylpyridines》 appeared in Journal of the American Chemical Society. The author of the article were Cao, Kangning; Tan, Siu Min; Lee, Richmond; Yang, Songwei; Jia, Hongshao; Zhao, Xiaowei; Qiao, Baokun; Jiang, Zhiyong. The article conveys some information:

Pyridine, one of the most important azaarenes, is ubiquitous in functional mols. The electronic properties of pyridine were exploited to trigger asym. transformations of prochiral species as a direct approach for accessing chiral pyridine derivatives However, the full potential of this synthetic strategy for the construction of enantioenriched γ-functionalized pyridines remains untapped. Here, the authors describe the first enantioselective addition of prochiral radicals to vinylpyridines under cooperative photoredox and asym. catalysis mediated by visible light. The enantioselective reductive couplings of vinylpyridines with aldehydes, ketones, and imines were achieved by employing a chiral Bronsted acid to activate the reaction partners and provide stereocontrol via H-bonding interactions. Valuable chiral γ-secondary/tertiary hydroxyl- and amino-substituted pyridines were obtained in high yields with good to excellent enantioselectivities.1-Thiophen-2-yl-ethanone(cas: 88-15-3Formula: C6H6OS) 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. Formula: C6H6OS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

《Synthesis of 4,6-dihydrothieno[3,4-b]thiophene》 was published in Journal of Organic Chemistry in 1966. These research results belong to MacDowell, Denis W. H.; Patrick, Timothy B.. Recommanded Product: 13250-82-3 The article mentions the following:

The synthesis of the title compound (I) along with several new 2,3-disubstituted thiophenes is described. N.M.R. and uv spectra of I are discussed with respect to possible ring strain in the thiophene nucleus. The experimental process involved the reaction of 2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3Recommanded Product: 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.Recommanded Product: 13250-82-3

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Reference of 1-Thiophen-2-yl-ethanoneIn 2019 ,《Thiophene and furan appended pyrazoline based fluorescent chemosensors for detection of Al3+ ion》 was published in Inorganic Chemistry Communications. The article was written by Rangasamy, Manjunath; Palaninathan, Kannan. The article contains the following contents:

Thiophene and furan appended pyrazoline receptors R1 and R2 were designed and synthesized for selective detection of Al3+ ion. Their photophys. properties were studied by UV-visible and fluorescence spectra. Surprisingly, both receptors R1 and R2 were displayed an excellent selective and sensitive response to Al3+ ion alone over other tested metal ions. Both the receptor R1 and R2 displays 1:1 stoichiometry for [R1-Al3+] and [R2-Al3+] complex and formed with an association constant of 1.84 × 104 M-1 and 1.92 × 104 M-1 resp. The limit of detection were calculated for R1 and R2 since 8.92 × 10-8 M and 1.04 × 10-7 M by the fluorescence titration method. The thiophene based receptor R1 exhibited superior chemosensor characteristics such as high intensity absorption and emission at longer wavelength as compered that of furan based receptor R2. In the part of experimental materials, we found many familiar compounds, such as 1-Thiophen-2-yl-ethanone(cas: 88-15-3Reference of 1-Thiophen-2-yl-ethanone)

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. Reference of 1-Thiophen-2-yl-ethanone

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

《Development and Process Intensification of an Efficient Flow-Cascade Reaction Sequence in the Synthesis of Afizagabar》 was written by Petho, Balint; Szilagyi, Gabor B.; Mengyel, Bela; Nagy, Tamas; Farkas, Ferenc; Katai-Fadgyas, Katalin; Volk, Balazs. Synthetic Route of C10H7FO2S And the article was included in Organic Process Research & Development on April 15 ,2022. The article conveys some information:

The traditional, batchwise pilot plant manufacturing process of a key intermediate drug candidate afizagabar (S44819) involved several kinds of transformations (besides a Dakin-West-type reaction, a ring closure and a keto reduction step). To mitigate some of the hazards associated with this sequence, a flow chem. approach was developed. First, a flow-cascade process was elaborated, which furnished the product with a throughput of 1.52 g/h with a HPLC purity of 95.6%. The bottleneck of the procedure in terms of output was the heterogeneous catalytic hydrogenation, therefore subsequent process intensification efforted primarily concentrated on this step. Finally, application of higher concentrations and an upscaled hydrogenation reactor combined with the corresponding adjustment of parameters of further reaction steps resulted in an efficient process with an effective product yield of 11.95 g/h and an increased HPLC purity (97.1%). The 4-step uninterrupted process described here was based on a newly developed heterogeneous flow reactor system and a custom-made liquid-liquid extractor, providing an instructive case study on handling hazardous processes in a safe and efficient way. After reading the article, we found that the author used Methyl 4-fluorobenzo[b]thiophene-2-carboxylate(cas: 220180-55-2Synthetic Route of C10H7FO2S)

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. Synthetic Route of C10H7FO2SIt 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.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Cai, Guiping; Yu, Wenying; Song, Dongmei; Zhang, Wenda; Guo, Jianpeng; Zhu, Jiawen; Ren, Yuhao; Kong, Lingyi published an article in European Journal of Medicinal Chemistry. The title of the article was 《Discovery of fluorescent coumarin-benzo[b]thiophene 1, 1-dioxide conjugates as mitochondria-targeting antitumor STAT3 inhibitors》.Safety of Methyl 4-fluorobenzo[b]thiophene-2-carboxylate The author mentioned the following in the article:

STAT3 has been extensively studied as a potential antitumor target. Though studies on regulating STAT3 mainly focus on the inhibition of STAT3 phosphorylation at Tyr705 residue, the phosphorylation at Ser727 residue of STAT3 protein is also closely associated with the mitochondrial import of STAT3 protein. N, N-diethyl-7-aminocoumarin is a fluorescent mitochondria-targeting probe. In this study, a series of STAT3 inhibitors were developed by connecting N, N-diethyl-7-aminocoumarin fluorophore with benzo [b]thiophene 1, 1-dioxide moiety. All designed compounds displayed potent anti-proliferative activity against cancer cells. The representative compound 7a(I) was mainly accumulated in mitochondria visualized by its fluorescence. STAT3 phosphorylation was inhibited by I at both Tyr705 and Ser727 residues. I inhibited STAT3 phosphorylation whereas had no influence on the phosphorylation levels of STAT1, JAK2, Src and Erk1/2, indicating good selectivity of I. Moreover, I down-regulated the expression of STAT3 target genes Bcl-2 and Cyclin D1, increased ROS production and remarkably reduced the mitochondrial membrane potential to induce mitochondrial apoptotic pathway. Furthermore, I in vivo suppressed breast cancer 4T1 implanted tumor growth. Taken together, these results highlighted that I might be a promising mitochondria-targeting STAT3 inhibitor for cancer therapy. The experimental part of the paper was very detailed, including the reaction process of Methyl 4-fluorobenzo[b]thiophene-2-carboxylate(cas: 220180-55-2Safety of Methyl 4-fluorobenzo[b]thiophene-2-carboxylate)

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. Safety of Methyl 4-fluorobenzo[b]thiophene-2-carboxylateIt 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.

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

In 1967,Acta Chemica Scandinavica (1947-1973) included an article by Gronowitz, Salo; Persson, Birgitta. Safety of 2-(Thiophen-3-yl)-1,3-dioxolane. The article was titled 《A convenient synthesis of thieno[2,3-b]thiophene》. The information in the text is summarized as follows:

Compound I (0.10 mole) in 30 ml. Et2O was treated dropwise with 89 ml. 1.2N BuLi in Et2O under N, the mixture refluxed 20 min., cooled in ice, 0.10 mole dry S added in small portions, the mixture refluxed 1 hr., cooled, 0.10 mole ClCH2CO2Me in 20 ml. Et2O added dropwise, and, after standing overnight, the mixture added to cold 2N HCl. The solution was extracted with Et2O, the extract dried, added dropwise to a solution of 6.9 g. Na in 200 ml. EtOH, the mixture refluxed 5 hrs., Et2O distilled, and the residue added to H2O and acidified to precipitate 94% II, m. 242-4° (AcOH). Crude II (9.2 g.), 5 g. Cu powder, and 100 ml. quinoline was heated carefully to 180° for 2 hrs. and to 225-30° for 24 hrs., the mixture distilled, the distillate acidified, and the insoluble oil distilled to give 78% title compound (III) b10 95°; picrate m. 135.5-6.5° (MeOH and EtOH). After reading the article, we found that the author used 2-(Thiophen-3-yl)-1,3-dioxolane(cas: 13250-82-3Safety of 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.Safety of 2-(Thiophen-3-yl)-1,3-dioxolane

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

In 2019,Applied Organometallic Chemistry included an article by Balamurugan, Gunasekaran; Balaji, Sundarraman; Ramesh, Rengan; Bhuvanesh, Nattamai S. P.. Category: benzothiophene. The article was titled 《Synthesis and Structures of Arene Ruthenium (II)-NHC Complexes: Efficient Catalytic α-alkylation of ketones via Hydrogen Auto Transfer Reaction》. The information in the text is summarized as follows:

A panel of six new arene Ru (II)-NHC complexes (NHC = 1,3-diethyl-(5,6-dimethyl)benzimidazolin-2-ylidene, 1,3-dicyclohexylmethyl-(5,6-dimethyl)benzimidazolin-2-ylidene and 1,3-dibenzyl-(5,6-dimethyl)benzimidazolin-2-ylidene) were synthesized from the transmetallation reaction of Ag-NHC with [(η6-arene)RuCl2]2 and characterized. The ruthenium (II)-NHC complexes were developed as effective catalysts for α-alkylation of ketones and synthesis of bioactive quinoline using primary/amino alcs. as coupling partners resp. The reactions were performed with 0.5 mol% catalyst load in 8 h under aerobic condition and the maximum yield was up to 96%. Besides, the different alkyl wingtips on NHC and arene moieties were studied to differentiate the catalytic robustness of the complexes in the transformations. The experimental process involved the reaction of 1-Thiophen-2-yl-ethanone(cas: 88-15-3Category: benzothiophene)

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. Category: benzothiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

In 2019,Angewandte Chemie, International Edition included an article by Falconnet, Alban; Magre, Marc; Maity, Bholanath; Cavallo, Luigi; Rueping, Magnus. COA of Formula: C6H6OS. The article was titled 《Asymmetric Magnesium-Catalyzed Hydroboration by Metal-Ligand Cooperative Catalysis》. The information in the text is summarized as follows:

Asym. catalysis with readily available, cheap, and nontoxic alk. earth metal catalysts represents a sustainable alternative to conventional synthesis methodologies. In this context, the authors describe the development of a 1st Mg(II)-catalyzed enantioselective hydroboration providing the products with excellent yields and enantioselectivities. NMR spectroscopy studies and DFT calculations provide insights into the reaction mechanism and the origin of the enantioselectivity which can be explained by a metal-ligand cooperative catalysis pathway involving a noninnocent ligand. The experimental process involved the reaction of 1-Thiophen-2-yl-ethanone(cas: 88-15-3COA of Formula: C6H6OS)

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