Month: February 2023

Substitution reactions of benzo[b]thiophene derivatives. Part VIII. Reactions of some 6-substituted compounds and of 4-chlorobenzo[b]thiophene and its 3-methyl derivative was written by Clark, Peter D.;Clarke, Kenneth;Scrowston, Richard M.;Sutton, Terence M.. And the article was included in Journal of Chemical Research, Synopses in 1978.Formula: C8H5ClS This article mentions the following:

Electrophilic substitution reactions (e.g., nitration, bromination, Friedel-Crafts acetylation) of the benzothiophene derivatives I (R = NHAc, OH, Me, Cl, R¹ = R² = H; R = Cl, R¹ = Me, R² = H; R = H, R¹ = H, Me, R² = Cl) were studied and new methods for the preparation of I (R = Cl, R¹ = Me, R² = H; R = H, R¹ = H, Me, R² = Cl) described. For I (R = NHAc, OH, R¹ = R² = H), the 2- and 7-positions are the most reactive in nitration and bromination although some substitution in the 5-position also occurred. For I (R = NHAc, R¹ = R² = H), Friedel-Crafts acetylation occurred in the 2- and 3-positions; Vilsmeier-Haack formylation gave either the N-formyl derivative or the amidine I (R = N:CHNMe₂, R¹ = R² = H), depending on the temperature I (R = Me, R¹ = R² = H) gave a mixture of the 2- and 3-substituted products (∼1:1) on nitration and bromination, but gave the 2-acetyl compound exclusively on acetylation. Substitution in I (R = Cl, R¹ = H, Me, R² = H) was confined to the 3- and 2-position resp., except that the former gave a mixture of the 2- and 3-acetyl derivatives on acetylation. I (R = H, R¹ = H, Me, R² = Cl) were both acetylated in the 2-position; the former gave a mixture of 2- and 3-substitution products on nitration and bromination. Bromination of I (R = H, R¹ = Me, R² = Cl) was confined to the Me group; nitration gave a mixture of the 2-nitro compound and the thiophenone II. In the experiment, the researchers used many compounds, for example, 6-Chlorobenzothiophene (cas: 66490-20-8Formula: C8H5ClS).

6-Chlorobenzothiophene (cas: 66490-20-8) 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.Formula: C8H5ClS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Metal-Free Dehydrogenative Double C-H Sulfuration To Access Thieno[2,3-b]indoles Using Elemental Sulfur was written by Liu, Jianming;Zhang, Yanyan;Yue, Yuanyuan;Wang, Zhixian;Shao, Huibin;Zhuo, Kelei;Lv, Qingzhang;Zhang, Zhiguo. And the article was included in Journal of Organic Chemistry in 2019.Recommanded Product: 3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one This article mentions the following:

A base-promoted metal-free approach for the synthesis of thieno[2,3-b]indole derivatives is reported. This method combined four C-H σ-bond cleavage reactions of two different kinds of C-H bonds and two C-S σ-bond formation processes. A series of thieno[2,3-b]indoles were obtained starting from 3-benzylindole derivatives with good yields and high regioselectivity, with the elemental sulfur serving as a cheap and readily available sulfur source. Good efficiency could be maintained even when the reaction was performed on a gram scale. A plausible mechanism was proposed on the basis of mechanistic studies. In the experiment, the researchers used many compounds, for example, 3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one (cas: 3988-77-0Recommanded Product: 3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one).

3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one (cas: 3988-77-0) belongs to benzothiophene derivatives. Benzothiophene scaffolds are of great importance due to its increased presence in bioactive molecules. It is also used in the manufacturing of dyes such as thioindigo.Recommanded Product: 3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis of Pyridine-SF₄-Isoxazolines Using the Functionality of trans-Tetrafluoro-λ⁶-sulfanyl Rodlike Linkers was written by Maruno, Koki;Hada, Kenshiro;Sumii, Yuji;Nagata, Osamu;Shibata, Norio. And the article was included in Organic Letters in 2022.Synthetic Route of C6H4S This article mentions the following:

The tetrafluoro-λ⁶-sulfanyl (SF₄) moiety has been relatively undeveloped since its discovery in the 1970s. In this study, we synthesized pyridine-SF₄-isoxazolines, in which the two heterocycles are connected by a rodlike trans-SF₄ linker, via the regioselective 1,3-dipolar cycloaddition of pyridine-SF₄-alkynes and nitrones in the presence of triethylamine. SF₄ linkers are a viable alternative to para-substituted benzenes, alkynes, and bicyclo[1.1.1]pentyl derivatives in drug design, and pyridine-SF₄-isoxazolines have potential applications in drug development. In the experiment, the researchers used many compounds, for example, 3-Ethynylthiophene (cas: 67237-53-0Synthetic Route of C6H4S).

3-Ethynylthiophene (cas: 67237-53-0) 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.Synthetic Route of C6H4S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

The substituent effects in thiophene compounds. I. Proton NMR and IR studies in methyl (substituted 2-thiophenecarboxylates) was written by Satonaka, Hajime. And the article was included in Bulletin of the Chemical Society of Japan in 1983.Reference of 28686-90-0 This article mentions the following:

The ¹H NMR and the IR CO group stretching frequencies of Me (3-, 4-, and 5-substituted 2-thiophenecarboxylate)s are observed Good linear correlations between the chem. shifts of the ring protons in Me (4- and 5-substituted 2-thiophenecarboxylate)s and those of the corresponding protons in substituted thiophenes were observed The coupling constants in Me (substituted 2-thiophenecarboxylate)s gave good correlations against the corresponding ones in substituted thiophenes. The IR carbonyl stretching frequencies in Me (5-substituted 2-thiophenecarboxylate)s were correlated reasonably well with the chem. shifts of 5-protons in 2-substituted thiophenes. The coupling constants in Me 2-thiophenecarboxylate series varied linearly with the electronegativities of the substituents. In the experiment, the researchers used many compounds, for example, Methyl 4-methylthiophene-2-carboxylate (cas: 28686-90-0Reference of 28686-90-0).

Methyl 4-methylthiophene-2-carboxylate (cas: 28686-90-0) 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 28686-90-0

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Decreasing the initial irreversible capacity loss by addition of cyclic sulfate as electrolyte additives was written by Sano, Atsushi;Maruyama, Satoshi. And the article was included in Journal of Power Sources in 2009.Category: benzothiophene This article mentions the following:

Initial irreversible capacity loss in graphite electrodes was suppressed by 1,3,2-dioxathiolane-2,2-dioxide and its derivatives (cyclic sulfates) in propylene carbonate (PC) containing electrolyte. Cyclic voltammetry (CV) showed that cyclic sulfates were decomposed at higher potentials than that for electrolyte solvents. In galvanostatic charge and discharge measurement, first cycle efficiency was increased from 58.2% to 90.5% by the addition of 1,3,2-dioxathiolane-2,2-dioxide. Passivation films formed by cyclic sulfates were observed by XPS, FT-IR, and pyrolysis/GC/MS (pyro/GC/MS). These results indicate that the surface was covered by a PEO like polymer with the inner layer comprised of Li₂S like compounds In the experiment, the researchers used many compounds, for example, 1,3,2-Dioxathiolane 2,2-dioxide (cas: 1072-53-3Category: benzothiophene).

1,3,2-Dioxathiolane 2,2-dioxide (cas: 1072-53-3) belongs to benzothiophene derivatives. Benzothiophene is used as starting material for the synthesis of bioactive molecules. 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.Category: benzothiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Enhanced photoconversion of 1,2-bis(2-methyl-1-benzothiophene-3-yl)perfluorocyclopentene in ionic liquid solutions was written by Soromenho, Mario R. C.;Siopa, Filipa;Afonso, Carlos A. M.;Esperanca, Jose M. S. S.. And the article was included in Journal of Photochemistry and Photobiology, A: Chemistry in 2018.Formula: C9H8S This article mentions the following:

An improved strategy for the photoinduced ring closure conversion of diarylethene, 1,2-bis(2-methyl-1-benzothiophene-3-yl)perfluorocyclopentene (BTF6), in ionic liquid solutions was investigated. The convertibility yield of the photochrome was monitored by UV-vis spectroscopy. Significant improvements of the convertibility yield were achieved in ionic liquid solutions in comparison with conventional organic solvents. These results open the door to the creation of new enriched photochromic systems based on ionic liquids In the experiment, the researchers used many compounds, for example, 2-Methylbenzo[b]thiophene (cas: 1195-14-8Formula: C9H8S).

2-Methylbenzo[b]thiophene (cas: 1195-14-8) 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 is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, sertaconazole, and also BTCP.Formula: C9H8S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Pyrolytic chemistry of thenyl benzoates was written by Chen, Ping-Shu;Chou, Chin-Hsing. And the article was included in Tetrahedron in 1996.Safety of 3-Ethylthiophene This article mentions the following:

Flash vacuum pyrolysis of 2- and 3-thenyl benzoates at temperatures in the range 550-750° and ca. 10^-2 torr gave several radical-derived products. The mechanism of formation of these pyrolysis products is proposed to involve 2- and 3-thenyl and Ph radicals. In the experiment, the researchers used many compounds, for example, 3-Ethylthiophene (cas: 1795-01-3Safety of 3-Ethylthiophene).

3-Ethylthiophene (cas: 1795-01-3) 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 is also used in the manufacturing of dyes such as thioindigo.Safety of 3-Ethylthiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Fly-ash:H₂O catalyzed aqueous phase cyclization of chalcones: synthesis of some substituted pyrazole-1-carbothioamides and spectral correlations in 3-(3,4-dimethylphenyl)-5-(substituted phenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamides was written by Thirunarayanan, G.;Sekar, K. G.. And the article was included in Organic Chemistry: An Indian Journal in 2013.Recommanded Product: 3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one This article mentions the following:

Substituted 1-thiocarbamoyl pyrazolines I (R¹ = Me, Ph, 4-MeOC₆H₄, 2-thienyl, 3,4-Me₂C₆H₃, etc.; R² = Ph, 4-MeOC₆H₄, 2-furyl, 2-thienyl, etc.) were synthesized by solvent-free aqueous phase fly-ash:H₂O catalyzed cyclization of chalcones R¹C(O)CH:CHR² and thiosemicarbazide in higher than 75% yields. The spectral data of the compounds I (R¹ = 3,4-Me₂C₆H₃; R² = Ph, 4-MeOC₆H₄, 2-BrC₆H₄, 4-BrC₆H₄, etc.) was correlated using single and multi-linear regression anal. In the experiment, the researchers used many compounds, for example, 3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one (cas: 3988-77-0Recommanded Product: 3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one).

3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one (cas: 3988-77-0) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The electrophilic substitution of benzothiophene systems is much less regioselective than that of indoles. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Recommanded Product: 3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Programmable, UV-printable dielectric elastomers actuate at low voltage without prestretch and supporting frames was written by Borayek, Ramadan;Zhang, Pengpeng;Willy, Habimana J.;Zedan, Mostafa;Zhu, Jian;Ding, Jun. And the article was included in ACS Applied Electronic Materials in 2020.Application In Synthesis of 2,5-Bis(5-(tert-butyl)benzo[d]oxazol-2-yl)thiophene This article mentions the following:

Dielec. elastomers are soft and perfect insulator polymers able to produce large strains with high energy d. under the effect of applied high voltage. However, their use in practical applications is hindered by the need for high voltage to actuate. Also, they need prestretching between rigid frames to produce out-of-plane shape changes, which may reduce their lifetime. Here, we synthesized a set of elastomers with high permittivity (from 20 to reach 60 at 10³ Hz), controllable thermal properties (T_g vary from -15 to -50°), and good mech. properties (Young’s modulus values between 0.48 and 0.2 MPa at 20% strain). Due to the high permittivity, an actuator made of the material was able to respond to a low voltage of 700 V and produce a 6.5% area strain for more than 10,000 cycles. Moreover, the elastomers were found to produce giant free-end bending displacements with prespecified bending direction (bend to the side of the pos. electrode) under a low elec. field, which we called programmable dielec. elastomers (PDE). Besides the aforementioned characteristics and performance, the formulated elastomers are suitable for UV-based three-dimensional (3D) printing. The printability of the elastomers allows fabricating programmable complex geometries to produce high deformations under relatively low elec. fields. In the experiment, the researchers used many compounds, for example, 2,5-Bis(5-(tert-butyl)benzo[d]oxazol-2-yl)thiophene (cas: 7128-64-5Application In Synthesis of 2,5-Bis(5-(tert-butyl)benzo[d]oxazol-2-yl)thiophene).

2,5-Bis(5-(tert-butyl)benzo[d]oxazol-2-yl)thiophene (cas: 7128-64-5) 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 is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, sertaconazole, and also BTCP.Application In Synthesis of 2,5-Bis(5-(tert-butyl)benzo[d]oxazol-2-yl)thiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Rh-Catalyzed Highly Enantioselective Synthesis of Aliphatic Sulfonyl Fluorides was written by Moku, Balakrishna;Fang, Wan-Yin;Leng, Jing;Li, Linxian;Zha, Gao-Feng;Rakesh, K. P.;Qin, Hua-Li. And the article was included in iScience in 2019.Reference of 113893-08-6 This article mentions the following:

Rh-catalyzed, highly enantioselective (up to 99.8% ee) synthesis of aliphatic sulfonyl fluorides (R)/(S)-RCH(R¹)CH₂SO₂F (R = Ph, dibenzo[b,d]thiophen-4-yl, thiophen-3-yl, etc.; R¹ = naphthalen-1-yl, dibenzo[b,d]furan-4-yl, benzo[b]thiophen-3-yl, etc.) was accomplished. This protocol provides a portal to a class of novel 2-aryl substituted chiral sulfonyl fluorides, which are otherwise extremely difficult to access. This asym. synthesis has the feature of mild conditions, excellent functional group compatibility, and wide substrate scope (51 examples) generating a wide array of structurally unique chiral β-arylated sulfonyl fluoride (R)-2-(dibenzo[b,d]thiophen-4-yl)-2-phenylethanesulfonyl fluoride for sulfur(VI) fluoride exchange (SuFEx) click reaction and drug discovery. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophen-3-ylboronic acid (cas: 113893-08-6Reference of 113893-08-6).

Benzo[b]thiophen-3-ylboronic acid (cas: 113893-08-6) 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.Reference of 113893-08-6

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem