Day: February 27, 2023

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

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 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

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

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

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

Synthesis of bulky-tailed sulfonamides incorporating pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-1(5H)-yl) moieties and evaluation of their carbonic anhydrases I, II, IV and IX inhibitory effects was written by Fares, Mohamed;Eladwy, Radwa A.;Nocentini, Alessio;Abd El Hadi, Soha R.;Ghabbour, Hazem A.;Abdel-Megeed, Ashraf;Eldehna, Wagdy M.;Abdel-Aziz, Hatem A.;Supuran, Claudiu T.. And the article was included in Bioorganic & Medicinal Chemistry in 2017.Reference of 3988-77-0 This article mentions the following:

Using celecoxib as lead, two novel series of sulfonamides incorporating the pyridotriazolopyrimidine scaffold have been synthesized and evaluated in vitro as inhibitors against four relevant human (h) carbonic anhydrases (CAs, EC 4.2.1.1), the cytosolic and ubiquitous hCA I and II as well as the transmembrane hCA IV and hCA IX. Most of the reported sulfonamides acted as efficient, low micromolar inhibitors of hCAI, II and IV, whereas they displayed higher efficacy in inhibiting the tumor-associated isoform hCA IX. Many derivates herein reported showed better hCA IX vs. hCA II selectivity ratios compared to celecoxib or acetazolamide. Considering isoform IX is a validated target for the diagnosis and treatment of hypoxic tumors, discovery of selective CA IX inhibitors represents a promising step to unveil more effective anticancer therapies. In the experiment, the researchers used many compounds, for example, 3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one (cas: 3988-77-0Reference of 3988-77-0).

3-Phenyl-1-(thiophen-2-yl)prop-2-en-1-one (cas: 3988-77-0) 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. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.Reference of 3988-77-0

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Detection and characterization of extractables in food packaging materials by GC-MS was written by Humston-Fulmer, Elizabeth M.;Binkley, Joe. And the article was included in LC-GC Europe in 2017.Computed Properties of C26H26N2O2S This article mentions the following:

Migration or leaching of analytes from packaging material is a concern for manufacturers and con- sumers because of the potential contamination of food and beverages. This leaching can impact the quality of the product, affect the integrity of the packaging material, and cause concern related to consumer health and product safety. To investigate analytes with the potential for leaching, an extrac- tion of a variety of food packaging or storage products, including sealable plastic bags and plastic food containers, was performed. Solvent was placed inside each packaging product for an extended period of time and then concentrated through evaporation before anal. General screening of this extract with nontargeted anal. techniques was used to understand what analytes were extracted and may have the potential to leach into the food. Gas chromatog. (GC) was used for separating analytes from each other and time-of-flight mass spectrometry (TOF-MS) provided full mass range spectral data. Nominal-mass TOF-MS data were acquired and searched against library databases for tentative identifications. High-resolution TOF-MS data were also acquired to add confidence to identi- fications with accurate mass information. Several analytes were determined and are highlighted here. In the experiment, the researchers used many compounds, for example, 2,5-Bis(5-(tert-butyl)benzo[d]oxazol-2-yl)thiophene (cas: 7128-64-5Computed Properties of C26H26N2O2S).

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 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.Computed Properties of C26H26N2O2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Rhodium(III)-Catalyzed Regioselective C-H Annulation and Alkenylation of 2-Pyridones with Terminal Alkynes was written by Li, Jiajie;Xu, Xin;Luo, Zhenli;Yao, Zhen;Yang, Ji;Zhang, Xin;Xu, Lijin;Wang, Peng;Shi, Qian. And the article was included in Advanced Synthesis & Catalysis in 2022.Related Products of 4298-52-6 This article mentions the following:

Cp*Rh(III)-catalyzed regioselective C-H annulation and alkenylation of 2-pyridones with terminal alkynes was developed. The cationic Cp*Rh(III) catalytic system containing FeCl₃ additive enables annulation of 1-(2-pyridyl)-2-pyridones with terminal alkynes, providing efficient access to 5,7-diarylated 2-quinolinones I [R = H, 4-Me, 3-Br, etc.; R¹ = H, 4-Me, 5-F, etc.; Ar = Ph, 2-MeC₆H₄, 2-naphthyl, etc.]. The reaction pathway could be switched to alkenylation with [Cp*RhCl₂]₂ as the catalyst, NaOAc as the additive and HOAc as the solvent, affording C6-alkenylated 1-(2-pyridyl)-2-pyridones II [R² = Ph, 3-MeC₆H₄, 2-naphthyl, etc.; R³ = H, 4-Me, 3-Br, etc.] in high yields. These protocols accommodated a wide range of substrates with good functional group compatibility. In the experiment, the researchers used many compounds, for example, 2-Ethynylthiophene (cas: 4298-52-6Related Products of 4298-52-6).

2-Ethynylthiophene (cas: 4298-52-6) belongs to benzothiophene derivatives. Benzothiophene scaffolds are of great importance due to its increased presence in bioactive molecules. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Related Products of 4298-52-6

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis of sulfur isosteres of cholanthrene was written by Faller, Pierre. And the article was included in Comptes Rendus des Seances de l’Academie des Sciences, Serie C: Sciences Chimiques in 1966.Reference of 5118-13-8 This article mentions the following:

The synthesis of I and II is described. 4-Bromobenzo[b]thiophene (III), b₂₀ 144° [1,1-dioxo derivative m. 147° (EtOH)], was prepared from ο-BrC₆H₄CHO via the following intermediates: 5-(ο-bromobenzylidene)rhodanine, m. 189° (EtOH); ο-BrC₆H₄CH:C(SH)CO₂H, m. 147°; [ο-BrC₆H₄CH:C(CO₂H)S]₂, m. 207° (EtOH); and 4-bromobenzo[b]-2-thienoic acid, m. 272° (EtOH). The Grignard reagent from I condensed with 4-cyanoindan and hydrolyzed gave IV, m. 88-9° (petroleum ether) [2,4-dinitrophenylhydrazone m. 234-5° (EtOH)], which subjected at 400-20° during 5-10 min. to an Elbs cyclodehydration under N yielded 10% II, m. 187-8° (EtOH-C₆H₆). 7-Br isomer of III yielded similarly V, m. 86.5° (petroleum ether) [2,4-dinitrophenylhydrazone m. 257° (EtOH-C₆H₆)], which was converted to 40% I, m. 172-3° (EtOH-C₆H₆); 2,4,7-trinitrofluorenone adduct m. 266° (absolute EtOH); picric acid adduct m. 149-50° (absolute EtOH); maleic anhydride adduct m. 251-2° (C₆H₆-petroleum ether). In the experiment, the researchers used many compounds, for example, 4-Bromobenzo[b]thiophene (cas: 5118-13-8Reference of 5118-13-8).

4-Bromobenzo[b]thiophene (cas: 5118-13-8) belongs to benzothiophene derivatives. Benzothiophene is relatively a stable molecule. The core structure is a part of various pharmaceutical substances and natural products. The different substitution patterns in these heterocycles offer new opportunities for drug discovery and other applications in materials science.Reference of 5118-13-8

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem