Category: benzothiophene

Electro-alkynylation: Intramolecular Rearrangement of Trialkynylorganoborates for Chemoselective C(sp²)-C(sp) Bond Formation was written by Music, Arif;Nuber, Constantin M.;Lemke, Yannick;Spiess, Philipp;Didier, Dorian. And the article was included in Organic Letters in 2021.Quality Control of Benzo[b]thiophen-3-ylboronic acid This article mentions the following:

An alternative and complementary transformation for the synthesis of aryl- and heteroaryl-substituted alkynes RCCR¹ (R = 4-methylphenyl, 2-(4-fluorophenyl)ethenyl, 1-benzyl-1H-pyrazol-4-yl, etc.; R¹ = t-Bu, 2-phenylethyl, 4-methoxyphenyl, etc.) is presented that relies on a chemoselective electrocoupling process. Tetraorganoborate substrates were logically designed and simply accessed by transmetalations using readily or com. available organotrifluoroborate salts RBF₃K. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophen-3-ylboronic acid (cas: 113893-08-6Quality Control of Benzo[b]thiophen-3-ylboronic acid).

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

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Alkali metal salts-assisted coupling reaction between fluorinated benzyl electrophiles and alkenylboronic acids was written by Xie, Wenna;Liu, Shiwen;Hammond, Gerald B.;Xu, Bo. And the article was included in New Journal of Chemistry in 2022.Computed Properties of C6H4S This article mentions the following:

Synthesis of ((aryl)trifluorobutenyl)arenes and ((aryl)fluorobutenyl)arenes (E)-ArCHR¹CH:CHR [Ar = Ph, 4-ClC₆H₄, 3-MeOC₆H₄, etc.; R = Ph, 4-MeC₆H₄, 4-MeOC₆H₄, etc.; R¹ = CF₃, CFH₂] via versatile transition metal-free cross-coupling reaction between fluorinated benzyl electrophiles and alkenylboronic acids in the presence of the equivalent amount of alkali metal salts such as K₃PO₄ was developed. This transition metal-free protocol gave good chem. yields for a wide range of substrates and demonstrates good functional group tolerance. In the experiment, the researchers used many compounds, for example, 2-Ethynylthiophene (cas: 4298-52-6Computed Properties of C6H4S).

2-Ethynylthiophene (cas: 4298-52-6) belongs to benzothiophene derivatives. Benzothiophenes are valuable heterocycles that are widely used in medicines, agrochemicals, and materials science. The different substitution patterns in these heterocycles offer new opportunities for drug discovery and other applications in materials science.Computed Properties of C6H4S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis of 2-(perfluoroalkyl)ethyl potassium sulfates based on perfluorinated Grignard reagents was written by Paterova, Jana;Skalicky, Martin;Rybackova, Marketa;Kvicalova, Magdalena;Cvacka, Josef;Kvicala, Jaroslav. And the article was included in Journal of Fluorine Chemistry in 2010.Quality Control of 1,3,2-Dioxathiolane 2,2-dioxide This article mentions the following:

The first example of nucleophilic substitution with perfluoroalkyl Grignard reagents on the sp³ carbon center is described. Thus, a series of organometals R_F-MgBr, prepared from perfluorinated alkyl iodides with alkyl group = C₄F₉, C₆F₁₃, C₈F₁₇, C₁₀F₂₁ and C₁₂F₂₅, reacted with 1,3,2-dioxathiolane-2,2-dioxide to afford the corresponding 2-(perfluoroalkyl)ethyl magnesium sulfates, which were isolated after metathesis to the corresponding potassium salts. In the model reaction, perfluorohexylmagnesium iodide was reacted with Me triflate yielding polyfluorinated alkane. The attempts to extend the reaction to 1,3,2-dioxathiane-2,2-dioxide were unsuccessful due to its inferior reactivity and only reduced polyfluoroalkane and the product of coupling were detected in the reaction mixture Polyfluorinated sulfates are easily hydrolyzed with hydrochloric or triflic acid to the corresponding alcs., which is an alternative to standard transformation of perfluoroalkyl iodides to 2-(perfluoroalkyl)ethanols. Quantum-chem. calculations of the PES of the reaction with both sulfur-containing heterocycles found that the failure of the reaction with 1,3,2-dioxathiane-2,2-dioxide is caused by higher activation energy of the process. In the experiment, the researchers used many compounds, for example, 1,3,2-Dioxathiolane 2,2-dioxide (cas: 1072-53-3Quality Control of 1,3,2-Dioxathiolane 2,2-dioxide).

1,3,2-Dioxathiolane 2,2-dioxide (cas: 1072-53-3) 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.Quality Control of 1,3,2-Dioxathiolane 2,2-dioxide

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis of Triarylmethanes via Palladium-Catalyzed Suzuki Coupling of Trimethylammonium Salts and Arylboronic Acids was written by Zhang, Zhenming;Wang, Hui;Qiu, Nianli;Kong, Yujing;Zeng, Wenjuan;Zhang, Yongquan;Zhao, Junfeng. And the article was included in Journal of Organic Chemistry in 2018.Application of 113893-08-6 This article mentions the following:

An efficient palladium-catalyzed Suzuki coupling of 1,1-diarylmethyl-trimethylammonium triflates with arylboronic acids is reported. This reaction offers a novel approach to triarylmethane derivatives in good to excellent yields with the palladium-catalyzed C-N bond cleavage as the key feature. Broad substrate scope regarding both reaction partners are observed Moreover, reactive functional groups such as vinyl and formyl groups are conserved in this transformation. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophen-3-ylboronic acid (cas: 113893-08-6Application of 113893-08-6).

Benzo[b]thiophen-3-ylboronic acid (cas: 113893-08-6) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The core structure is a part of various pharmaceutical substances and natural products. 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.Application of 113893-08-6

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Solvothermal liquefaction of waste polyurethane using supercritical toluene in presence of noble metal catalysts was written by Ghalandari, Vahab;Banivaheb, Soudeh;Peterson, Jessica;Smith, Hunter;Reza, M. Toufiq. And the article was included in AIChE Journal in 2022.Name: 2,5-Bis(5-(tert-butyl)benzo[d]oxazol-2-yl)thiophene This article mentions the following:

Solvothermal liquefaction (STL) is a thermochem. conversion method that uses sub-or supercritical solvents to convert waste plastics like waste polyurethane (PU) into value-added chems. This study aimed to evaluate catalytic STL utilizing toluene as a solvent for depolymerization of waste PU into valuable products. The effect of catalyst type (Pt/C, Pd/C, and Ru/C), catalyst loading (0-10 wt%), STL reaction temperature (330°C, 350°C, and 370°C), STL residence time (1, 3, and 5 h), and hydrogen loading (25, 50, and 75 bar) on STL conversion were studied. Result showed that Ru/C outperformed Pt/C and Pd/C and the STL conversion reached to as high as 87.2%. The concentrations of nitrogen-containing components like aniline and p-aminotoluene were increased with the increase of Ru/C loading and STL reaction temperature In the experiment, the researchers used many compounds, for example, 2,5-Bis(5-(tert-butyl)benzo[d]oxazol-2-yl)thiophene (cas: 7128-64-5Name: 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. Functionalized benzothiophenes are important constructs found in molecules with wide ranging biological activity and in organic materials. 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.Name: 2,5-Bis(5-(tert-butyl)benzo[d]oxazol-2-yl)thiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis of 6-substituted thianaphthenes was written by Hansch, Corwin;Schmidhalter, Beno. And the article was included in Journal of Organic Chemistry in 1955.Synthetic Route of C8H5ClS This article mentions the following:

When 2,4-HS(H₂N)C₆H₃Et is dehydrogenated according to H., et al. (C.A. 45, 6542c), at 445°, 81% 6-amino-thianaphthene (I), m. 114-15°, is obtained (Bz derivative, m. 129.5-30°). I picrate, yellow needles, m. 198-200° (decomposition). Diazotizing 4.37 g. I in 25 cc. H₂O and 10 cc. HCl with 2.76 g. NaNO₂ in 5 cc. H₂O at below 5° and heating the diazo solution 0.5 h. on a water bath with 8.8 g. CuCl in 25 cc. HCl and 7.5 cc. H₂O give 3.46 g. 6-chloro analog, m. 42-3° [picrate (II), m. 74-5°]. Diazotizing 3 g. I and refluxing the solution with 20 cc. H₂SO₄ and 15 cc. H₂O give 0.5 g. 6-hydroxy analog (III), m. 102-2.5° (p-nitrobenzoate, prepared by refluxing III with p-O₂NC₆H₄COCl and C₅H₅N 1 h., m. 149-50°). Diazotizing 10 g. I and adding the solution to a mixture of 9.8 g. CuCl in 15 cc. H₂O, 12.4 g. NaCN in 35 cc. H₂O, and 50 cc. PhMe at 0°, stirring the mixture 1 h., and heating it 2 h. at 60° give 3.8 g. 6-cyano analog, b_0.1 105-6°, m. 41.5-2°, which (0.5 g.), refluxed with 5 cc. 75% H₂SO₄, gives 463 mg. corresponding acid, m. 215-16°. Diazotizing 15.4 g. 2,4-(H₂N)ClC₆H₃CO₂H in 50 cc. H₂O and 20 cc. HCl at 0° with 6.9 g. NaNO₂ in 15 cc. H₂O, pouring the solution into 24 g. Na₂S.9H₂O and 3.6 g. NaOH in 35 cc. H₂O at below 5°, keeping the mixture several hrs., and acidifying it give 7.82 g. [5,2-Cl(HO₂C) C₆H₃]₂S₂, m. 309-11° (decomposition), which (7 g.) is refluxed 0.5 h. with 11.5 g. Na₂CO₃ and 8.5 g. Na₂S₂O₄ in 85 cc. H₂O, then CH₂ClCO₂Na (from 8.5 g. acid) in 110 cc. H₂O is added, and the mixture refluxed 1 h., giving 7.24 g. 4,2-Cl(HO₂C)C₆H₃SCH₂CO₂H (IV), m. 190-5° (decomposition). Refluxing 3 g. IV with 1.5 g. NaOAc and 8 cc. Ac₂O 1 h., diluting the mixture with Et₂O, and evaporating the washed (NaHCO₃) Et₂O solution leave 2.14 g. oil which, refluxed with 50 cc. 10% NaOH and steam distilled, gives 1 g. 3-hydroxy-6-chlorothianaphthene (V), m. 143°. Refluxing 0.8 g. V in 12 cc. AcOH 1 h. with 2 g. Zn dust, making the solution alk., steam distilling it, and treating the distilled oil with picric acid give 0.6 g. II. Refluxing 5 g. 4-oxo-4,5,6,7-tetrahydrothianaphthene (VI) in 25 cc. C₅H₅N and 25 cc. absolute EtOH 8 h. with 5 g. H₂NOH.HCl gives 4.8 g. VI oxime (VII), m. 131-2°. Dry HCl is passed into 3.8 g. VII in 25 cc. AcOH and 4 cc. Ac₂O 0.5 h. at 20° and 2 h. at 100°, the cooled mixture diluted with H₂O and extracted with Et₂O, giving 1.1 g. 4-aminothianaphthene (VIII) (Ac derivative, m. 133-4°). Diazotizing VIII and treating the diazo solution with CuCl in HCl give 4-chlorothianaphthene, isolated as picrate, m. 135-6°. In the experiment, the researchers used many compounds, for example, 6-Chlorobenzothiophene (cas: 66490-20-8Synthetic Route of C8H5ClS).

6-Chlorobenzothiophene (cas: 66490-20-8) belongs to benzothiophene derivatives. Functionalized benzothiophenes are important constructs found in molecules with wide ranging biological activity and in organic materials. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Synthetic Route of C8H5ClS

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

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

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

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