Category: benzothiophene

Condensed thiophene ring systems. XV. Preparation and reactions of 2- and 3-(secondary amino)benzo[b]thiophenes was written by Chippendale, Kevan E.;Iddon, Brian;Suschitzky, Hans;Taylor, David S.. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1974.Recommanded Product: 2,3-Dibromobenzo[b]thiophene This article mentions the following:

2,3-Dibromobenzo[b]thiophene with piperidine, pyr-rolidine, and morpholine gave 21-74% of the corresponding 2-(secondary amino)benzo[b] thiophenes, e.g. I, which underwent C-3 acetylation. I with Br and HNO3-AcOH gave the 3-bromo and 3,6-dinitro derivatives, resp. Nitrosation of 3-piperidinobenzo-[b]thiophene gave the 2-oxime of benzo[b]thiophene-2,3-dione. The reactions of the p-tolysulfonylhydrazones of 2-morpho-linobenzo[b]thiophene-3- and 3-piperidinobenzo[b]thiophene-2-carboxaldehyde with NaOMe in [MeO(CH2)2]2O are reported. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Recommanded Product: 2,3-Dibromobenzo[b]thiophene).

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. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, and sertaconazole, and also BTCP.Recommanded Product: 2,3-Dibromobenzo[b]thiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis, properties and application in optical memory of a new photochromic diarylethene was written by Liu, Ming;Li, Wei;Pu, Shouzhi;Liu, Gang;Cui, Shiqiang. And the article was included in Key Engineering Materials in 2011.Category: benzothiophene This article mentions the following:

A new photochromic diarylethene compound, 1-[2-methyl-3-benzothiophene]-2-[5-(3-chlorobenzene)-2-methyl-3-thienyl]perfluorocyclopentene, was synthesized and its photochromism and photo-induced anisotropy was investigated. It showed good photochromism and functioned as an effective fluorescent photoswitch in solution In hexane, the open ring isomer of the diarylethene exhibited relatively strong fluorescence at 417 nm when excited at 315 nm. In PMMA film, the open ring form of diarylethene also showed good photochromism. In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9Category: benzothiophene).

3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9) 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.Category: benzothiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Toward Asymmetric Synthesis of Pentaorganosilicates was written by van der Boon, Leon J. P.;Fuku-en, Shin-ichi;Slootweg, J. Chris;Lammertsma, Koop;Ehlers, Andreas W.. And the article was included in Topics in Catalysis in 2018.Electric Literature of C8H4Br2S This article mentions the following:

Introducing chiral silicon centers was explored for the asym. Rh-catalyzed cyclization of dihydrosilanes to enantiomerically enriched spirosilanes as targets to enable access to enantiostable pentacoordinate silicates. The steric rigidity required in such systems demands the presence of two naphthyl or benzo[b]thiophene groups. The synthetic approach to the expanded spirosilanes extends Takai’s method (Kuninobu et al. in Angew Chem Int Ed 52(5):1520-1522, 2013) for the synthesis of spirosilabifluorenes in which both a Si-H and a C-H bond of a dihydrosilane are activated by a rhodium catalyst. The expanded dihydrosilanes were obtained from halogenated aromatic precursors. Their asym. cyclization to the spirosilanes were conducted with [Rh(cod)Cl]₂ in the presence of the chiral bidentate phosphine ligands (R)-BINAP, (R)-MeO-BIPHEP, and (R)-SEGPHOS, including derivatives with P-(3,5-t-Bu-4-MeO)-Ph (DTBM) groups. The highest enantiomeric excess of 84% was obtained for 11,11′-spirobi[benzo[b]-naphtho[2,1-d]silole] with the DTBM-SEGPHOS ligand. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Electric Literature of C8H4Br2S).

2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7) belongs to benzothiophene derivatives. Benzothiophene scaffolds are of great importance due to its increased presence in bioactive molecules. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, and sertaconazole, and also BTCP.Electric Literature of C8H4Br2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Upgrading of thiophenic compounds from fuels over a silver-modified MoO₃ catalyst under ambient conditions was written by Miao, Guang;Chong, Peng;Yang, Cuiting;Liu, Zewei;Yu, Hao;Dong, Lei;Li, Guoqing;Xiao, Jing. And the article was included in Fuel in 2021.SDS of cas: 6287-82-7 This article mentions the following:

The demand for heterocyclic sulfur compounds is increasingly in fine chem. industry, where the thiophenic sulfur impurities in fuels can be a potential recyclable feedstock. In this work, the catalytic upgrading of thiophenic sulfur compounds over a silver-modified MoO₃ catalyst under ambient conditions was reported. Br₂ and H₂O₂/HBr were used to convert thiophenic compounds in alkane and alc. solutions The conversion of various thiophenic compounds (thiophene, benzothiophene and dibenzothiophene) to the corresponding bromides reached up to 81.6 ∼ 99.8%. The bromination path undergoes electrophilic substitution mechanism, and the transformation of mono- to dibromides is identified as the rate-determining step. The introduction of MoAg₂O₄ phase on MoO₃ is rationalized to boost the conversion of mono-bromothiophene, which results in the selectivity of 2,5-dibromothiophene increased from 10% to over 50%. The optimized silver loading was 10% due to its high thiophene conversion and selectivity of dibromides. Silver modification of MoO₃ rods not only stabilized the textural property of catalysts but also improved its bromination activity compared to the bulk MoO₃ indicated by SEM and FTIR characterization. D. functional theory (DFT) calculation suggested that the formation of 2-bromothiphene and 2,5-dibromothiophene were preferred on the MoO₃(111) and MoAg₂O₄(111) sites, resp. The catalytic upgrading approach paves the way for the efficient utilization of thiophenic sulfur impurities in fuels to their value-added under mild conditions. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7SDS of cas: 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.SDS of cas: 6287-82-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Substitution reactions of 2- and 3-methylthianaphthene was written by Shirley, David A.;Danzig, Morris J.;Canter, Frank C.. And the article was included in Journal of the American Chemical Society in 1953.Formula: C9H7BrS This article mentions the following:

2-Methylthianaphthene (I) in 30 cc. CHCl₃ (ice bath) treated dropwise with Br in CHCl₃ yielded 7.0 g. 2-methyl-3-bromothianaphthene (II), m. 42-2.5°. II converted to the Grignard reagent (considerable MeI required to initiate the reaction) and carbonated yielded 50% 2-methyl-3-thianaphthenecarboxylic acid (III), m. 194-5°. III was desulfurized to α-phenylbutyric acid, m. 33.5-35°; amide, m. 85-6°. I (10 g.) in 65 cc. AcOH (ice bath) treated during 5 min. with 30 cc. concentrated HNO₃, the mixture let stand 30 min. in the ice bath and filtered yielded 5.75 g. 2-methyl-3-nitro-thianaphthene (IV), m. 98-8.5°. IV (5 g.) reduced in AcOH-Ac₂O over Raney Ni at 50 lb./sq. in. H yielded 2.73 g. 2-methyl-3-acetamidothianaphthene (V), m. 186-6.5°. Desulfurization of V yielded N-acetyl-1-phenylpropylamine, m. 77-8°. 3-Methylthianaphthene (VI) (6.6 g.) in 30 cc. Et₂O treated slowly with 0.045 mol BuLi in Et₂O, the mixture refluxed 45 min., carbonated with Dry Ice, hydrolyzed, treated with dilute HCl, and the Et₂O extracts evaporated yielded 5.1 g. 3-methyl-2-thianaphthenecarboxylic acid (VII), m. 244.5-46°. VII treated with SOCl₂ and the acid chloride with NH₃ yielded 70% of the amide (VIII), m. 181-3°. Desulfurization of VIII yielded 85% β-phenylbutyramide, m. 105-6°; p-nitro derivative, m. 164°. VI (5 g.) in 10 cc. AcOH treated with 10 cc. each of HNO₃ and AcOH, the mixture let stand 15 h. at room temperature, and poured into water yielded 1.65 g. 2-nitro-3-methylthianaphthene (IX), m. 148-9°. Reduction of IX gave 55% of the acetamido (X) compound, m. 182.5-83°, which on alk. hydrolysis gave 2-phenylpropylamine; picrate, m. 184-5°; N-Bz derivative, m. 87.5-88°. IX in Et₂O reduced over Raney Ni at 50 lb./sq. in., the Et₂O evaporated, and the residue treated with BzCl and alkali yielded 2-benzamido-3-methylthianaphthene, m. 167.5-70°. In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9Formula: C9H7BrS).

3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9) 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 is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, and sertaconazole, and also BTCP.Formula: C9H7BrS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Geometry and Aromaticity in Highly Strained Heterocyclic Allenes: Characterization of a 2,3-Didehydro-2H-thiopyran was written by Nikitina, Asya F.;Sheridan, Robert S.. And the article was included in Organic Letters in 2005.COA of Formula: C9H5NS This article mentions the following:

The highly strained cyclic allene 2,3-didehydro-2H-thiopyran was generated by irradiation of matrix-isolated 2-benzothienylchlorocarbene and characterized by IR and UV/vis spectroscopy, in situ trapping, and DFT modeling. Calculations indicate that the allenic moiety in this system, although less aromatic in character, is relatively more stable than in the corresponding oxa system. It is suggested that the thio ring system can more readily accommodate the allenic geometry. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9COA of Formula: C9H5NS).

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.COA of Formula: C9H5NS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Reversibly Photo-Switchable Nucleosides: Synthesis and Photochromic Properties of Diarylethene-Functionalized 7-Deazaadenosine Derivatives was written by Singer, Marco;Jaeschke, Andres. And the article was included in Journal of the American Chemical Society in 2010.Application In Synthesis of 3-Bromo-2-methylbenzo[b]thiophene This article mentions the following:

Photochromic nucleosides, e.g. I, were designed that combine the structural features and mol. recognition properties of nucleic acids with the light-sensitivity of diaryl-ethenes. Target compounds, e.g. I, consist of a 7-deazaadenosine unit that is linked to a thiophene as the second aryl functionality via a 1,2-cyclopentenyl linker. These nucleoside analogs undergo a reversible electro-cyclic rearrangement, generating strongly colored closed-ring isomers upon irradiation with UV-light, while exposure to light in the visible range triggers the cyclo-reversion to the colorless opened-ring form. UV-vis spectroscopy, HPLC, and ¹H NMR measurements revealed recognition of complementary thymidine and up to 97% conversion to the thermally stable closed-ring isomers after illumination with UV-light. The required wavelength for ring closure was found to vary depending on the substituents attached to the thiophene moiety. In a first design step, we used this important feature of diaryl-ethenes, e.g. I, to shift the switching wavelength from initially 300 nm to 405 nm. In a second step, we generated a pair of orthogonal switches, differing enough in their resp. switching wavelengths to be controlled independently in the same sample. Finally, a mol. switch was developed that showed both photochromism and acidichromism, thereby illustrating the possibility to gate the spectral properties to multiple stimuli. These new photochromic nucleosides represent useful building blocks for the generation of light-sensitive nucleic acids either by inducing conformational changes upon isomerization or by exploring the different spectral properties of the closed and opened isomers, for example, for use as reversible fluorescence quenchers. In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9Application In Synthesis of 3-Bromo-2-methylbenzo[b]thiophene).

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 also used in the manufacturing of dyes such as thioindigo.Application In Synthesis of 3-Bromo-2-methylbenzo[b]thiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis and photochromic activity of a new diarylethene bearing benzo[b]thiophene unit was written by Hossain, Mohammed Kamrul;Sanaullah, Abul Fazal Mohammad;Uddin, Mohammad Helal. And the article was included in Pakistan Journal of Scientific and Industrial Research, Series A: Physical Sciences in 2013.Synthetic Route of C9H7BrS This article mentions the following:

The synthesis of new photochromic compound 3-[2-(3,5-bismethoxymethoxymethylthiophen-2-yl)-3,3,4,4,5,5-hexafluorocyclopent-1-enyl]-2-methyl-benzo[b]thiophene was reported. In multistep synthesis from 2,4-dibromothiophene, benzo[b]thiophene was synthesized. This product exhibited photochromic properties upon irradiation with UV and visible light. In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9Synthetic Route of C9H7BrS).

3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9) belongs to benzothiophene derivatives. Benzothiophene scaffolds are of great importance due to its increased presence in bioactive molecules. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, and sertaconazole, and also BTCP.Synthetic Route of C9H7BrS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Palladium-catalyzed synthesis of nitriles from N-phthaloyl hydrazones was written by Ano, Yusuke;Higashino, Masaya;Yamada, Yuki;Chatani, Naoto. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2022.Application of 55219-11-9 This article mentions the following:

The Pd-catalyzed transformation of N-phthaloyl hydrazones into nitriles RC≡N [R = 3-pyridyl, 4-MeC₆H₄, 2-naphthyl, etc.] and R(Me)C=CHC≡N involving the cleavage of an N-N bond was reported. The use of N-heterocyclic carbene as a ligand was essential for the success of the reaction. N-Phthaloyl hydrazones prepared from aromatic aldehydes or cyclobutanones were applicable to this transformation, which gaves aryl nitriles RC≡N or alkenyl nitriles R(Me)C=CHC≡N, resp. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9Application of 55219-11-9).

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

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Mechanistic Switch in Dual Gold Catalysis of Diynes: C(sp³)-H Activation through Bifurcation-Vinylidene versus Carbene Pathways was written by Hansmann, Max M.;Rudolph, Matthias;Rominger, Frank;Hashmi, A. Stephen K.. And the article was included in Angewandte Chemie, International Edition in 2013.Recommanded Product: 2,3-Dibromobenzo[b]thiophene This article mentions the following:

Gold-catalyzed cycloisomerization of 2,3-diethynylthiophenes with terminal CC bond to give indanothiophenes and fluorenothiophenes. E.g., reaction of 2-ethynyl-3-(oct-1-yn-1-yl)thiophene and 5 mol% IPrAuNTf₂ (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, Tf = trifluoromethylsulfonyl) in dry toluene at 70° gave 7-propyl-6,7-dihydro-5H-indeno[5,6-b]thiophene in 54% yield. Variation of the backbone of the diyne system opens up a pathway for the intramol. C(SP³)-H activation event. Based on theor. work it is postulated that a switch in selectivity along a bifurcation pathway, for the first time leading to products through σ,π dual activation and a 6-endo diyne cyclization. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Recommanded Product: 2,3-Dibromobenzo[b]thiophene).

2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7) 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. The different substitution patterns in these heterocycles offer new opportunities for drug discovery and other applications in materials science.Recommanded Product: 2,3-Dibromobenzo[b]thiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem