Day: January 4, 2023

A synthesis of benzo[b]naphtho[2,3-d]thiophene derivatives via benzo[b]thiophene-2,3-quinodimethane intermediates was written by Kano, Shinzo;Mochizuki, Naoki;Yuasa, Yoko;Hibino, Satoshi;Shibuya, Shiroshi. And the article was included in Heterocycles in 1982.Synthetic Route of C9H7BrS This article mentions the following:

The thermal decomposition of 2-alkyl-3-(α-hydroxybenzyl)benzo[b]thiophenes I (R = H, Me; R¹ = H, Ph; R² = OMe, H) gave the resp. benzonaphthothiophenes II; fused compounds III (R = Me, Ph; R¹ = H, OMe) were obtained by the thermal decomposition of benzothiophenes IV. I (R = R¹ = H, R² = OMe) was heated 5 min at 410° to give II (R = R¹ = H, R² = OMe). 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 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.Synthetic Route of C9H7BrS

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Competitive cyclization of singlet and triplet nitrenes. Part 7. Reaction paths of 2-azidophenyl benzothienyl sulfides was written by Hawkins, David G.;Meth-Cohn, Otto;Suschitzky, Hans. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1979.Product Details of 10243-15-9 This article mentions the following:

Thermal decomposition of I (R = Me) and II gave III and IV, resp., via spirobenzothiazoline intermediates. 2-(2,3-Dihydro-3-benzo[b]thienyl)benzothiazole and 2-(3-benzo[b]thienyl)benzothiazole were also obtained from the thermal decomposition of I (R = Me). Similar thermolysis of I (R = H) resulted in polymer formation only, indicating the necessity of the Me substituent. 2-Azidophenyl 3-(2,5-dimethylthienyl) sulfide, however, gave 2-methylbenzothiazole. These various reaction paths are rationalized by comparison with those of the related thienyl sulfides. In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9Product Details of 10243-15-9).

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. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.Product Details of 10243-15-9

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis, spectra, and reactions of some S-alkylthiophenium salts was written by Acheson, Richard M.;Harrison, Derek R.. And the article was included in Journal of the Chemical Society [Section] C: Organic in 1970.COA of Formula: C8H4Br2S This article mentions the following:

S-Alkylthiophenium, -benzo[b]thiophenium and -dibenzo[b,d]thiophenium salts were prepared by treatment of the corresponding thiophenes with alkyl halides in the presence of AgBF4 or similar reagents. Their uv spectra resemble those of the corresponding sulfoxides and sulfones, rather than those of the parent thiophene. The NMR spectrum of 3-bromo-1-ethylbenzo[b]thiophenium tetrafluoroborate and those of similar compounds show that the Et groups appear as ABX3 systems, which were computer-simulated. The S-alkyl groups are putatively not coplanar with the S-containing rings. In the mass spectrometer the S-alkyl group is very readily lost, but expansion of the thiophene ring also occurs. The salts are powerful alkylating agents. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7COA of Formula: 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 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.COA of Formula: C8H4Br2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis of functionalized benzothiophenes and dibenzothiophenes by two fold Heck and subsequent 6π-electrocyclization reactions of 2,3-dibromothiophenes and 2,3-dibromobenzothiophenes was written by Tengho Toguem, Serge-Mitherand;Malik, Imran;Hussain, Munawar;Iqbal, Jamshed;Villinger, Alexander;Langer, Peter. And the article was included in Tetrahedron in 2013.Electric Literature of C8H4Br2S This article mentions the following:

Benzothiophenes and dibenzothiophenes were prepared by two-fold Heck reactions of 2,3-dibromothiophene and 2,3-dibromobenzothiophene, resp., followed by thermal 6π-electrocyclization and dehydrogenative aromatization reactions. The Heck reaction of 2,3-dibromothiophene and 2,3-dibromobenzothiophene with 1 equiv of alkenes proceeded with different regioselectivities and afforded 2-alkenylthiophenes and 3-alkenylbenzothiophenes. 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 is used as starting material for the synthesis of bioactive molecules. 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.Electric Literature of C8H4Br2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

A novel route to isoannulated heteroaromatic compounds 2. – The dipole route to furo/thieno pyrroles and α-pyridones, and their benzo derivatives was written by Bussenius, Jorg;Laber, Norbert;Muller, Thomas;Eberbach, Wolfgang. And the article was included in Chemische Berichte in 1994.COA of Formula: C8H4Br2S This article mentions the following:

A new methodol. involving 1,7-dipolar cyclizations of conjugated dipoles followed by a multistep rearrangement affording ring-contracted products has been employed for the synthesis of various examples of the title compounds Under different thermolysis conditions the annulated alkynyl nitrones are converted into isoannulated pyrroles and α-pyridones, resp., with yields up to 90%. The product distribution is strongly influenced by the nature of a terminal substituent R, hence supporting a mechanism with oxo carbenes as central intermediates which undergo either 6-π cyclization to the pyrrole systems of Wolff rearrangement leading to conjugates ketenes, the precursors of the observed α-pyridones. Diels-Alder reactions were performed with a benzofuropyridone derivative, naphthopyridone derivative, as well as with the corresponding dihydronaphtho compounds Whereas tert-Bu derivatives are rather un-reactive against dienophiles, they are easily transformed into cyclic imides under the influence of oxygen and light suggesting the formation and subsequent [4+2] cycloaddition of ¹O₂ as important steps. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7COA of Formula: C8H4Br2S).

2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7) 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. The different substitution patterns in these heterocycles offer new opportunities for drug discovery and other applications in materials science.COA of Formula: C8H4Br2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Sodium halides as the source of electrophilic halogens in green synthesis of 3-halo- and 3,n-dihalobenzo[b]thiophenes was written by Kesharwani, Tanay;Kornman, Cory;Tonnaer, Amanda;Hayes, Amanda;Kim, Seoyoung;Dahal, Nikesh;Romero, Ralf;Royappa, Andrew. And the article was included in Tetrahedron in 2018.Synthetic Route of C8H4Br2S This article mentions the following:

A convenient methodol. for the synthesis of mono- and di-halogenated benzo[b]thiophenes I (R = (CH₂)₃CH₃, C₆H₅, 4-H₃COC₆H₄, SiMe₃, cyclohex-2-en-1-yl, etc.; X = Cl, Br, I; X¹ = H, 4-Br, 5-Br, 6-Br, 7-Br), which utilizes copper(II) sulfate pentahydrate and various sodium halides NaX in the presence of substituted 2-alkynylthioanisoles 2-CH₃S-X¹C₆H₃CCR is described herein. The proposed method is facile, uses ethanol as a green solvent, and results in uniquely substituted benzo[b]thiophene I structures with isolated yields up to 96%. The most useful component of this methodol. is the selective introduction of bromine atoms at every available position (2-7) around the benzo[b]thiophene ring, while keeping position 3 occupied by a specific halogen atom such as Cl, Br or I. Aromatic halogens are useful reactive handles and therefore, the selective introduction of halogens at specific positions would be valuable in the targeted synthesis of bioactive mols. and complex organic materials via metal-catalyzed cross coupling reactions. This work is a novel approach towards the synthesis of dihalo substituted benzo[b]thiophenes I core structures, which provides a superior alternative to the current methods discussed herein. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Synthetic Route of C8H4Br2S).

2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7) 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 zileuton, raloxifene, and sertaconazole, and also BTCP.Synthetic Route of C8H4Br2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Structure-activity relationships of arylimidazopyridine cardiotonics; synthesis and inotropic activity of benzthienyl- and naphthyl-substituted imidazopyridines and purines was written by Robertson, David W.;Krushinski, Joseph H.;Beedle, E. E.;Wyss, V.;Pollock, G. Don;Hayes, J. Scott. And the article was included in European Journal of Medicinal Chemistry in 1986.Recommanded Product: 6-Methoxybenzo[b]thiophene This article mentions the following:

Several ring-annelated analogs I [A, B = N, CH; R, R¹ = H, OMe (1- or 2-naphthyl derivatives)] and II (A, B = N, CH; R = H, OMe; X = S, O, or SO; Y = CH₂, O; z = 1-2) of the potent inotrope isomazole (LY175326) were prepared and evaluated for their inotropic activities. The dihydrobenzthienyl analog of isomazole II (A = N; B = CH; R = OMe; X = SO; Y = CH₂; z = 1) [103811-54-7], was prepared via a 9-step sequence starting from 3-methoxybenzenethiol  [15570-12-4]. All other analogs were synthesized in 2-3 steps from readily available starting materials. In the naphthyl series, only the 2-naphthyl analogs had significant in vitro activity, and the imidazo[4,5-c]pyridine analog [98410-79-8] possessed greater intrinsic potency than either the analogous imidazo[4,5-b]pyridine [89574-50-5] or purine analog [98410-77-6]. I.v. administration of 8 mg/kg of the 2-naphthyl analog I ( A = N; B = CH; R = 3-OMe; R¹ = 6-OMe) [98410-71-0] markedly increased contractility (+ 140 %) while having relatively minor effects on heart rate (+ 14 %); mean arterial blood pressure was not changed. The dihydrobenzthienyl analog of isomazole was the most potent compound tested, with an ED₅₀ in anesthetized dogs of 2.0 mg/kg. In the experiment, the researchers used many compounds, for example, 6-Methoxybenzo[b]thiophene (cas: 90560-10-4Recommanded Product: 6-Methoxybenzo[b]thiophene).

6-Methoxybenzo[b]thiophene (cas: 90560-10-4) 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.Recommanded Product: 6-Methoxybenzo[b]thiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Novel 2-Carbonylbenzo[b]thiophene 1,1-Dioxide Derivatives as Potent Inhibitors of STAT3 Signaling Pathway was written by Ji, Peng;Xu, Xin;Ma, Shuhua;Fan, Junchao;Zhou, Qiang;Mao, Xinliang;Qiao, Chunhua. And the article was included in ACS Medicinal Chemistry Letters in 2015.Formula: C10H7BrO2S This article mentions the following:

Signal transducer and activator of transcription 3 (STAT3) is considered to be an attractive therapeutic target for cancer therapy. In this study, a series of 2-carbonylbenzo[b]thiophene 1,1-dioxide derivatives (CBT) were designed to inhibit the STAT3 SH2 domain phosphorylation site Try 705. The authors demonstrated that incorporation of basic flexible groups through amide bond linkage to benzo[b]thiophene 1,1-dioxide (BTP) achieved compounds with higher antiproliferative potency than BTP itself. The most potent compound I, as indicated from luciferase reporter gene assay, inhibited the STAT3 pathway by decreasing the phosphorylation level of STAT3 Tyr705, while the phosphorylation level of other upstream tyrosine kinases in this pathway was not significantly inhibited. Compound I was also shown to trigger ROS generation and accumulation, thus consequently attributed partially to the observed cell apoptosis. This study provided important structural information for the development of inhibitors targeting the STAT3 pathway. In the experiment, the researchers used many compounds, for example, Methyl 5-bromobenzo[b]thiophene-2-carboxylate (cas: 7312-11-0Formula: C10H7BrO2S).

Methyl 5-bromobenzo[b]thiophene-2-carboxylate (cas: 7312-11-0) belongs to benzothiophene derivatives. Benzothiophene finds use in research as a starting material for the synthesis of larger, usually bioactive structures. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, sertaconazole, and also BTCP.Formula: C10H7BrO2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Regioisomeric Effects of Donor-Acceptor-Acceptor’ Small-Molecule Donors on the Open Circuit Voltage of Organic Photovoltaics was written by Che, Xiaozhou;Chung, Chin-Lung;Liu, Xiao;Chou, Shu-Hua;Liu, Yi-Hung;Wong, Ken-Tsung;Forrest, Stephen R.. And the article was included in Advanced Materials (Weinheim, Germany) in 2016.Name: 2,3-Dibromobenzo[b]thiophene This article mentions the following:

We have elucidated the structure-property performance relationships of highly dipolar d-a-a’ small mols. used in organic donor-acceptor heterojunctions. Specifically, the mols. introduced with anti and syn asym. heteroacenes as coplanar donors of BTDC were used to investigate mol. regioisomeric effects on photogeneration efficiency when blended with fullerene acceptors. Both mols. pack in an antiparallel arrangement to achieve a centroymmetric dimer, leading to a net dipole moment of zero. The synBTDC with a shorter backbone conjugation length exhibits a reduced intra- and intermol. charge transfer compared with antiBTDC. An optimized OPV based on antiBTDC:C70 blend achieves VOC = 0.91 ^α 0.01 V, FF = 0.56 ^α 0.01, and PCE = 7.2 ^α 0.3%. Despite the reduced charge transfer and blue-shifted absorption which lead to smaller JSC, synBTDC shows a lower HOMO energy with higher VOC = 1.01 ^α 0.3 V, with a power conversion efficiency of 6.1 ^α 0.3%. The design of PYDC leads to a further enhanced VOC = 1.06 ^α 0.01 V due to the reduced quinoidal character of pyrimidine. We find that the VOC of the d-a-a’ donor:C70 devices is a function of the donor conjugation length: a reduction of backbone conjugation lowers the HOMO level for both groups of mols. with embedded benzothiadiazole or pyrimidine central “a” unit, leading to an enlarged donor-acceptor HOMO-LUMO gap and a larger VOC. Shortening the alkyl chains, or raising their LUMO energy for more complete exciton dissociation may lead to further improvements in FF, and ultimately the device performance. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Name: 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. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.Name: 2,3-Dibromobenzo[b]thiophene

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

The effects of heteroaryl ring on the photochromism of diarylethenes with a naphthalene moiety was written by Wang, Renjie;Pu, Shouzhi;Liu, Gang;Cui, Shiqiang;Li, Hui. And the article was included in Tetrahedron Letters in 2013.HPLC of Formula: 10243-15-9 This article mentions the following:

Three new asym. naphthalene-containing diarylethenes with different heteroaryl groups have been synthesized to investigate the heteroaryl effects on their properties. The three diarylethenes exhibited distinctive photochromism with good thermal stability, which may be attributed to the different heteroaryl effects. Their cycloreversion quantum yields increased in the order of 2-methylbenzofuran < 2-methylbenzothiophene < 1,2-dimethylindole, while the cyclization quantum yields exhibited a reverse trend. Compared to indole and benzothiophene, the benzofuran moiety could effectively shift the absorption maximum to a shorter wavelength and notably enhance the cyclization quantum yield and fluorescence quantum yield of the diarylethene. The results indicated that the category of heteroaryl groups played a vital role during the process of photoisomerization of naphthalene-containing diarylethene derivatives In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9HPLC of Formula: 10243-15-9).

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 also used in the manufacturing of dyes such as thioindigo.HPLC of Formula: 10243-15-9

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem