Day: January 6, 2023

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

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

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

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

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

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

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

Diastereoselective self-assembly of a triple-stranded europium helicate with light modulated chiroptical properties was written by Zhang, Zhihui;Zhou, Yanyan;Gao, Ting;Yan, Pengfei;Zou, Xiaoyan;Li, Hongfeng. And the article was included in Dalton Transactions in 2021.Formula: C9H7BrS This article mentions the following:

Chiroptical photoswitches are of increasing interest for their potential in advanced information technologies. Herein, an achiral bis-β-diketonate ligand (o-L) with a photoresponsive diarylethene moiety as a linker was designed, which co-assembled with Eu³⁺ ions and R- and S-bis(diphenylphosphoryl)-1,10-binaphthyl (R/S-BINAPO) as chiral ancillaries to form dinuclear triple-stranded helicates, [Eu₂(o-L)₃(R/S-BINAPO)₂]. The helicates in the enantiopure form were confirmed by ¹H, ¹⁹F, ³¹P NMR and DOSY NMR analyses. Also, the mirror-image CD and CPL spectra also demonstrate the existence of stable ground- and excited-state chiralities in solution When exposed to alternate UV and visible light, the helicates showed reversible color variations from colorless to purple, followed by the presence of light-triggered quadruple optical and chiroptical outputs, named CD, PL, CPL and g_lum switches. With these light-modulated optical outputs, the possibility for the fabrication of IMPLICATION and INHIBIT logic gates is discussed. 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 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.Formula: C9H7BrS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Discovery of LSZ102, a Potent, Orally Bioavailable Selective Estrogen Receptor Degrader (SERD) for the Treatment of Estrogen Receptor Positive Breast Cancer was written by Tria, George S.;Abrams, Tinya;Baird, Jason;Burks, Heather E.;Firestone, Brant;Gaither, L. Alex;Hamann, Lawrence G.;He, Guo;Kirby, Christina A.;Kim, Sunkyu;Lombardo, Franco;Macchi, Kaitlin J.;McDonnell, Donald P.;Mishina, Yuji;Norris, John D.;Nunez, Jill;Springer, Clayton;Sun, Yingchuan;Thomsen, Noel M.;Wang, Chunrong;Wang, Jianling;Yu, Bing;Tiong-Yip, Choi-Lai;Peukert, Stefan. And the article was included in Journal of Medicinal Chemistry in 2018.Formula: C9H8OS This article mentions the following:

In breast cancer, estrogen receptor alpha (ERα) pos. cancer accounts for approx. 74% of all diagnoses, and in these settings, it is a primary driver of cell proliferation. Treatment of ERα pos. breast cancer has long relied on endocrine therapies such as selective estrogen receptor modulators, aromatase inhibitors, and selective estrogen receptor degraders (SERDs). The steroid-based anti-estrogen fulvestrant, the only approved SERD, is effective in patients who have not previously been treated with endocrine therapy as well as in patients who have progressed after receiving other endocrine therapies. Its efficacy, however, may be limited due to its poor physicochem. properties. THe authors describe the design and synthesis of a series of potent benzothiophene-containing compounds that exhibit oral bioavailability and preclin. activity as SERDs. This article culminates in the identification of LSZ102 (I), a compound in clin. development for the treatment of ERα pos. breast cancer. In the experiment, the researchers used many compounds, for example, 6-Methoxybenzo[b]thiophene (cas: 90560-10-4Formula: C9H8OS).

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

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

An efficient novel synthesis of β-(azuleno[1,2-b]benzothienyl)- and β-(azuleno[2,1-b]benzothienyl)-α,β-unsaturated ketones by the tropylium ion-mediated intramolecular furan ring-opening reaction and X-ray investigation of methyl ketone derivative was written by Yamamura, Kimiaki;Houda, Yuuko;Hashimoto, Masao;Kimura, Takatomo;Kamezawa, Makoto;Otani, Takehiko. And the article was included in Organic & Biomolecular Chemistry in 2004.Product Details of 6287-82-7 This article mentions the following:

Intramol. reaction of 2-tropylio-3-(5-substituted 2-furyl)benzothiophenes, prepared from the corresponding 2-cycloheptatrienyl-3-(5-substituted 2-furyl)benzothiophenes, afforded the β-(azuleno[1,2-b]benzothienyl)-α,β-unsaturated ketones, e.g., I, which are otherwise difficult to obtain, in moderate yields. The reaction involves a ring-opening process of the furan ring by intramol. attack of the tropylium ion onto the 2-position of the furan ring. Similarly, β-(azuleno[2,1-b]benzothienyl)-α,β-unsaturated ketones were obtained from the corresponding 3-tropylio-2-(5-substituted 2-furyl)benzothiophenes albeit in lower yields. The mol. and crystal structures of the Me ketone derivative, 8a, are discussed on the basis of X-ray structure anal. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Product Details of 6287-82-7).

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

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem