Month: February 2023

Structurally Diverse π-Extended Conjugated Polycarbo- and Heterocycles through Pd-Catalyzed Autotandem Cascades was written by Barroso, Raquel;Cabal, Maria-Paz;Badia-Laino, Rosana;Valdes, Carlos. And the article was included in Chemistry – A European Journal in 2015.Formula: C8H4Br2S This article mentions the following:

The Pd-catalyzed reaction between 2,2′-dibromobiphenyls and related systems with tosylhydrazones gives rise to new π-extended conjugated polycarbo- and heterocycles through an autotandem process involving a cross-coupling reaction followed by an intramol. Heck cyclization. The reaction shows wide scope regarding both coupling partners. Cyclic and acyclic tosylhydrazones can participate in the process. Addnl., a variety of aromatic and heteroaromatic dibromoderivatives have been employed, leading to an array of diverse scaffolds featuring a fluorene or acridine central nucleus, and containing binaphthyl, thiophene, benzothiophene and indole moieties. The application to appropriate tetrabrominated systems led to greater structural complexity through two consecutive autotandem cascades. The photophys. properties of selected compounds were studied through their absorption and emission spectra. Fluorescence mols. featuring very high quantum yields were identified, showing the potential of this methodol. in the development of mols. with interesting optoelectronic properties. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Formula: C8H4Br2S).

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. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, and sertaconazole, and also BTCP.Formula: C8H4Br2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Research on photochromic materials with synthesis and properties of 1-(2-methyl-3-benzothiophene)-2-[2-methyl-5-(3-cyanophenyl)-3-thienyl]perfluorocyclopentene was written by Liao, Guanming;Zheng, Chunhong;Pu, Shouzhi. And the article was included in Applied Mechanics and Materials in 2014.Application of 10243-15-9 This article mentions the following:

An asym. photochromic diarylethene, 1-(2-Methyl-3-benzothiophene)-2-[2-methyl-5-(3-cyanophenyl)-3-thienyl]perfluorocyclopentene (I) was synthesized and its photochromic and fluorescent properties in hexane solution as well as PMMA films were investigated in detail. Exptl. results showed that compound I exhibited remarkable photochromism. Upon irradiation with 297 nm UV light, the colorless solution of compound I turned to violet with a new visible absorption band centered at 535 nm (ε = 1.08 x 10⁴ L mol^-1 cm^-1) attributable to the closed-ring isomer II. The emission intensity of diarylethene I in a photostationary state was quenched to calculated 32% in hexane and 43% in PMMA film. In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9Application 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.Application of 10243-15-9

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis of 2,3-Disubstituted Benzo[b]thiophenes via Palladium-Catalyzed Coupling and Electrophilic Cyclization of Terminal Acetylenes was written by Yue, Dawei;Larock, Richard C.. And the article was included in Journal of Organic Chemistry in 2002.Name: 2,3-Dibromobenzo[b]thiophene This article mentions the following:

2,3-Disubstituted benzo[b]thiophenes, e.g., I, have been prepared in excellent yields via coupling of terminal acetylenes with com. available o-iodothioanisole in the presence of a palladium catalyst and subsequent electrophilic cyclization of the resulting o-(1-alkynyl)thioanisole derivatives I₂, Br₂, NBS, p-O₂NC₆H₄SCl, and PhSeCl have been utilized as electrophiles. Aryl-, vinyl-, and alkyl-substituted terminal acetylenes undergo this coupling and cyclization to produce excellent yields of benzo[b]thiophenes. (Trimethylsilyl)acetylene also undergoes this coupling/cyclization process with I₂, NBS, and the sulfur and selenium electrophiles to afford the corresponding 2-(trimethylsilyl)benzo[b]thiophenes. However, cyclization of the silyl-containing thioanisole using Br₂ affords 2,3-dibromobenzo[b]thiophene. 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. 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.Name: 2,3-Dibromobenzo[b]thiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Benzothiophenes. II.Ultraviolet and nuclear magnetic resonance (N.M.R.) spectra of some methoxybenzothiophenes was written by Angeloni, Annino Sante;Tramontini, Maurilio. And the article was included in Annali di Chimica (Rome, Italy) in 1963.Reference of 90560-10-4 This article mentions the following:

Ultraviolet spectra of 3-, 4-, 5-, 6-, and 7-methoxybenzothiophenes are presented. They are essentially similar to those of the Me derivatives Spectra of the methoxythioanisoles are presented in terms of their possible contribution to the benzothiophene chromophore. In the N.M.R. spectra, τ MeO = 5.79-6.22, and the Me derivatives have τ Me = 7.43-7.63. The o-, m-, and p-methoxythiophenetoles show a singlet from the MeO at about 6.20 τ, a CH₂ quadruplet at about 7.20 τ, and a Me triplet at about 8.70 τ. Similarly, the methoxythioanisoles have r MeO of ∼6.2 and τ Me of ∼7.6. In 5-methoxybenzothiophene, the MeO group has τ = 5.79; this is clearly lower than the other derivatives, which are about the same as the τ values for MeO in the methoxythioanisoles and closer to τ = 5.92 of anisole itself. Distillation of the crude mixture from the cyclization of m-methoxyphenyl 2,2-dimethoxyethyl sulfide gave ∼35% of a mixture of 4- and 6-methoxybenzothiophene, b₁₆ = 105-144°. The mixture was chromatographed on alumina. The 1st fractions gave the picrate of 4-methoxybenzothiophene, m. 108-9° (10%) (alc.). The same compound was obtained by the methylation of 4-hydroxybenzothiophene. The last fractions gave 15% of 6-methoxybenzothiophene, m. 38-9°. o-Methoxythiophenetole was prepared (66%) by treating an alk. solution of o-MeOC₆H₃SH with (EtO)₂SO₂. Repeated distillation at 123° at 12 mm. gave the product, m-Methoxythiophenetole, b₁₂ 125° (65%), was prepared similarly. In the experiment, the researchers used many compounds, for example, 6-Methoxybenzo[b]thiophene (cas: 90560-10-4Reference of 90560-10-4).

6-Methoxybenzo[b]thiophene (cas: 90560-10-4) 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.Reference of 90560-10-4

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

One-Pot Transformation of Carboxylic Acids into Nitriles was written by Miyagi, Kotaro;Moriyama, Katsuhiko;Togo, Hideo. And the article was included in European Journal of Organic Chemistry in 2013.Quality Control of Benzo[b]thiophene-2-carbonitrile This article mentions the following:

A variety of aromatic and aliphatic carboxylic acids were smoothly converted into the corresponding nitriles in good yields in a one-pot procedure by treatment with Et iodide/K₂CO₃/18-crown-6, followed by sodium diisobutyl-tert-butoxyaluminum hydride (SDBBA-H), and finally treatment with mol. iodine or 1,3-diiodo-5,5-dimethylhydantoin (DIH), and aqueous ammonia. This method is useful for the conversion of various aromatic and aliphatic carboxylic acids into the corresponding nitriles in a one-pot procedure. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9Quality Control of Benzo[b]thiophene-2-carbonitrile).

Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9) 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 raloxifene, zileuton, sertaconazole, and also BTCP.Quality Control of Benzo[b]thiophene-2-carbonitrile

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Efficient synthesis of chiral 2,3-dihydro-benzo[b]thiophene 1,1-dioxides via Rh-catalyzed hydrogenation was written by Liu, Gongyi;Zhang, Heng;Huang, Yi;Han, Zhengyu;Liu, Gang;Liu, Yuanhua;Dong, Xiu-Qin;Zhang, Xumu. And the article was included in Chemical Science in 2019.Reference of 6287-82-7 This article mentions the following:

Rh-catalyzed asym. hydrogenation of prochiral substituted benzo[b]thiophene 1,1-dioxides was successfully developed, affording various chiral 2,3-dihydrobenzo[b]thiophene 1,1-dioxides I (R = H, 6-MeO; R¹ = C₆H₅, 4-MeOC₆H₄, 4-FC₆H₄, etc.; R² = C₆H₅, 4-MeOC₆H₄, 3-H₃CC₆H₄, etc.) with high yields and excellent enantioselectivities (up to 99% yield and >99% ee). In particular, for challenging substrates, such as aryl substituted substrates with sterically hindered groups and alkyl substituted substrates, the reaction proceeded smoothly in catalytic system with excellent results. The gram-scale asym. hydrogenation proceeded well with 99% yield and 99% ee in the presence of 0.02 mol% (S/C = 5000) catalyst loading. The possible hydrogen-bonding interaction between the substrate and the ligand may play an important role in achieving high reactivity and excellent enantioselectivity. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Reference of 6287-82-7).

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. The different substitution patterns in these heterocycles offer new opportunities for drug discovery and other applications in materials science.Reference of 6287-82-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

New catalytic properties of iron complexes. Dehydration of amides to nitriles was written by Zhou, Shaolin;Addis, Daniele;Das, Shoubhik;Junge, Kathrin;Beller, Matthias. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2009.Application In Synthesis of Benzo[b]thiophene-2-carbonitrile This article mentions the following:

Various iron carbonyl clusters such as Fe₂(CO)₉ or [Et₃NH][HFe₃(CO)₁₁] catalyzed the dehydration of amides into the corresponding nitriles in the presence of silanes in high yields. This novel protocol showed good functional group tolerance and wide substrate scope. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9Application In Synthesis of Benzo[b]thiophene-2-carbonitrile).

Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9) 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 raloxifene, zileuton, and sertaconazole, and also BTCP.Application In Synthesis of Benzo[b]thiophene-2-carbonitrile

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Enantioselective synthesis of acyclic monohydrosilanes by steric hindrance assisted C-H silylation was written by Mu, Delong;Pan, Shuqiong;Wang, Xiaoyu;Liao, Xiaoyun;Huang, Yong;Chen, Jiean. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2022.COA of Formula: C9H8OS This article mentions the following:

Herein, a rhodium-catalyzed desymmetrization of dihydrosilanes with heterocyclic compounds via intermol. dehydrogenative C-H silylation is developed. The strategy tolerates a variety of thianaphthene and thiophene derivatives, giving rise to a wide range of silicon-stereogenic acyclic monohydrosilanes. Several rare skeletons featuring bis-silicon-stereogenic centers were also designed to enhance the library’s diversity further. Preliminary mechanistic studies reveal that the surrounding spatial environment of the Si-center plays a crucial role in enabling intermol. C-H silylation preferentially. In the experiment, the researchers used many compounds, for example, 6-Methoxybenzo[b]thiophene (cas: 90560-10-4COA of Formula: C9H8OS).

6-Methoxybenzo[b]thiophene (cas: 90560-10-4) 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.COA of Formula: C9H8OS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Chloro-oxime derivatives as novel small molecule chaperone amplifiers was written by Zhou, Yuefen;Vu, Khang;Chen, Yongsheng;Pham, John;Brady, Thomas;Liu, Gang;Chen, Jinhua;Nam, Joonwoo;Murali Mohan Reddy, P. S.;Au, Qingyan;Yoon, Il Sang;Tremblay, Marie-Helene;Yip, Gary;Cher, Charmian;Zhang, Bin;Barber, Jack R.;Ng, Shi Chung. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2009.SDS of cas: 55219-11-9 This article mentions the following:

Chloro-oxime derivatives were investigated as novel small mol. chaperone amplifiers. Lead optimization led to the discovery of compounds that displayed potent HSF1 activation activity, significant cytoprotection in MG-132 stress, ER stress and PolyQ stress cell models (EC₅₀ < 10 μM). 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. Benzothiophene is relatively a stable molecule. The electrophilic substitution of benzothiophene systems is much less regioselective than that of indoles. 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: 55219-11-9

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

A novel synthesis of benzo[b]thiophene was written by Liao, Zutai;Lv, Xuehao;Tao, Ming. And the article was included in Research on Chemical Intermediates in 2013.Reference of 55219-11-9 This article mentions the following:

A convenient method of preparation of benzo[b]thiophene by the using 2-chlorobenzaldehyde and 2-mercaptoacetonitrile as starting materials was reported. The process comprises two steps, neither of which was reported previously. The reactions in this work are clean and efficient. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9Reference of 55219-11-9).

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

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem