Category: 6287-82-7

Mechanistic study on rearrangement cascades starting from annulated 2-aza-hepta-2,4-dienyl-6-ynyl anions: formation of aniline and azepine derivatives was written by Lyaskovskyy, Volodymyr;Froehlich, Roland;Wuerthwein, Ernst-Ulrich. And the article was included in Chemistry – A European Journal in 2007.Related Products of 6287-82-7 This article mentions the following:

Deprotonation of benzothiophene-derived alkynyl imine 11 with lithium diisopropylamide (LDA) and subsequent transmetalation with ZnCl₂ etherate furnished azepine 12 upon aqueous workup. Similarly, alkynyl benzaldimine 1a gave a mixture of benzazepine 13 and naphthylamine 14. Allylic benzonitriles 15a,b reacted to produce naphthylamine 16 upon deprotonation with LDA at room temperature In an analogous manner, imino benzonitrile 17 may be converted into 4-amino isoquinoline 18 by means of an intramol. nucleophilic attack on the nitrile function upon treatment with LDA. The allylic benzonitriles 19a,b were prepared by LDA treatment of alkynyl imine 11. They were further converted to amino dibenzothiophene 20 by LDA deprotonation and aqueous workup. These various transformations represent tile key steps of a multistep reaction cascade, which was previously postulated on the basis of quantum chem. calculations Thus, all features of this complex rearrangement mechanism could now be confirmed exptl. DFT calculations support the lower reactivity of zinc species in the ring-opening step compared to the lithium intermediates. All new compounds were completely characterized by spectroscopic data, including X-ray diffraction studies for the key compounds 12, 19a, and 20. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Related Products of 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. It is also used in the manufacturing of dyes such as thioindigo.Related Products of 6287-82-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

The diyne reaction of 3,3′-bis(phenylethynyl)-2,2′-bithiophene derivatives via rhodium complexes. A novel approach to condensed benzo[2,1-b:3,4-b’]dithiophenes was written by Dahlmann, Uwe;Neidlein, Richard. And the article was included in Helvetica Chimica Acta in 1997.COA of Formula: C8H4Br2S This article mentions the following:

Benzodithiophenes I [R₂ = H₂, (CH)₄; R¹ = H, Ph, CO₂Me] and benzotrithiophenes II [R, R¹ = H; R₂, R¹₂ = (CH)₄] were prepared Thus, treating bis(phenylethynyl)bithiophenes III [R, R¹ = H; R₂, R¹₂ = (CH)₄], easily available via Pd(II)-catalyzed alkynylation of the corresponding dibromobithiophenes, with [Rh(PPh₃)₃Cl] yields cyclic Rh complexes which smoothly react with appropriate R²CCR² or S to give the target compounds in good yields. 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 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.COA of Formula: C8H4Br2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Benzo[b]thiophene Fusion Enhances Local Borepin Aromaticity in Polycyclic Heteroaromatic Compounds was written by Messersmith, Reid E.;Yadav, Sangeeta;Siegler, Maxime A.;Ottosson, Henrik;Tovar, John D.. And the article was included in Journal of Organic Chemistry in 2017.Reference of 6287-82-7 This article mentions the following:

This report documents the synthesis, characterization, and computational evaluation of two isomeric borepin-containing polycyclic aromatics The syntheses of these two isomers involved sym. disubstituted alkynes that were reduced to Z-olefins followed by borepin formation either through an isolable stannocycle intermediate or directly from the alkene via the trapping of a transient dilithio intermediate. Comparisons of their magnetic, crystallog., and computational characterization to literature compounds gave valuable insights about the aromaticity of these sym. fused [b,f]borepins. The fusion of benzo[b]thiophene units to the central borepin cores forced a high degree of local aromaticity within the borepin moieties relative to other known borepin-based polycyclic aromatics Each isomer had unique electronic responses in the presence of fluoride anions. The exptl. data demonstrate that the local borepin rings in these two compounds have a relatively high amount of aromatic character. Results from quantum chem. calculations provide a more comprehensive understanding of local and global aromatic characters of various rings in fused ring systems built upon boron heterocycles. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Reference 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. It is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, sertaconazole, and also BTCP.Reference of 6287-82-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

“Lock and Key Control” of Photochromic Reactivity by Controlling the Oxidation/Reduction State was written by Li, Xiaochuan;Ma, Yuzhen;Wang, Bingcai;Li, Gongan. And the article was included in Organic Letters in 2008.Related Products of 6287-82-7 This article mentions the following:

A photochem. active triangle terarylene was synthesized and the photochromic behavior was investigated. Its photochromic reactivity can be strongly suppressed by selected oxidization of the sulfur atoms in the mols. Reactivated photochromic reactivity was obtained by deoxidization of the S,S-dioxide moieties. The suppressed photoactivity of the oxidation state was attributed to the stronger intramol. hydrogen bonding interactions. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Related Products of 6287-82-7).

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.Related Products of 6287-82-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Toward Soluble 5,10-Diheterotruxenes: Synthesis and Reactivity of 5,10-Dioxatruxenes, 5,10-Dithiatruxenes, and 5,10-Diazatruxenes was written by Gorski, Krzysztof;Mech-Piskorz, Justyna;Lesniewska, Barbara;Pietraszkiewicz, Oksana;Pietraszkiewicz, Marek. And the article was included in Journal of Organic Chemistry in 2020.Formula: C8H4Br2S This article mentions the following:

The following work presents three general approaches allowing, for the first time, the synthesis of 5,10-diheterotruxene derivatives I (x = O, S, NEt) containing two identical heteroatoms, namely, oxygen OOC, nitrogen NNC, or sulfur SSC. Two of described pathways involve the photocyclization of the corresponding triene II as a key step leading to a heptacyclic aromatic system. The third approach is based on the acidic condensation between ninhydrin and benzo[b]heteroole III. Typical functionalizations of the 5,10-diheterotruxenes I core have also been presented. In addition, the article discusses the advantages and limitations of the three suggested paths for receiving specific 5,10-diheterotruxene derivatives I because the universal method suitable for obtaining mols. with any type of heteroatoms is not known so far. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7Formula: C8H4Br2S).

2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7) belongs to benzothiophene derivatives. Functionalized benzothiophenes are important constructs found in molecules with wide ranging biological activity and in organic materials. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.Formula: C8H4Br2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Polymerization of thiophene derivatives. IV. The formation of some 9-thia-1,2- and 9-thia-3,4-benzofluorene derivatives was written by Davies, W.;James, F. C.;Middleton, S.;Porter, Q. N.. And the article was included in Journal of the Chemical Society in 1955.COA of Formula: C8H4Br2S This article mentions the following:

The self-condensation of thianaphthene dioxide derivatives was studied. New syntheses have been developed for related polycyclic sulfones and sulfoxides. 10,11-Dihydro-9-thia-3,4-benzofluorene 9,9-dioxide (I) was heated 20 min. to yield an oil which was chromatographed on alumina with C₆H₆ and recrystallized to give blue fluorescent 9-thia-1,2-benzofluorene 9,9-dioxide (II), m. 195.5-6° (from C₆H₆). Fusion of II with KOH at 400° for 5 min. gives only a phenolic oil. Desulfurization of II occurs on refluxing 8 h. with Raney Ni in EtOH to give 2-phenylnaphthalene, m. 102-3°. II with LiAlH₄ yields 10,11-dihydro-9-thia-1,2-benzofluorene 9,9-dioxide (III), m. 157-8° (from EtOH). III with Br yields 3,4-dibromo-10,11-dihydro-9-thia-1,2-benzofluorene 9,9-dioxide (IV), m. 226-6.5°. Refluxing IV in pyridine gives II. On heating I with PCl₅, 2-chloro-9-thia-3,4-benzofluorene 9,9-dioxide (V), m. 294-5° (from MeOCH₂CH₂OH) is formed along with 1,2-dichloro-1,2,10,11-tetrahydro-9-thia-3,4-benzofluorene 9,9-dioxide (VI), m. 173.5-4°. Heating VI yields 9-thia-3,4-benzofluorene 9,9-dioxide (VII), m. 234°. Heating 3-chlorothianaphthene 1,1-dioxide gives 2,11-dichloro-10,11-dihydro-9-thia-3,4-benzofluorene 9,9-dioxide (VIII), m. 270-1° (from C₆H₆). Refluxing VIII with pyridine gives V. I with Br gives 2-bromo-9-thia-3,4-benzofluorene 9,9-dioxide (IX), m. 309-10°, and 1,2-dibromo-1,2,10,11-tetrahydro-9-thia-3,4-benzofluorene 9,9-dioxide (X), m. 185.5-6°. Refluxing X with pyridine gives VII. 3-Bromothianaphthene 1,1-dioxide is heated at 300° for 0.5 h. to give IX. 5-Bromothianaphthene in HOAc with H₂O₂ yields 5-bromothianaphthene 1,1-dioxide (XI), m. 144-4.5°. XI is refluxed for 3 h. with o-C₆H₄Cl₂ to give 2′,6-dibromo-10,11-dihydro-9-thia-3,4-benzofluorene 9,9-dioxide (XII), m. 228-9° (from EtOH). XII with Br yields 1,2,2′,6-tetrabromo-1,2,10,11-tetrahydro-9-thia-3,4-benzofluorene 9,9-dioxide (XIII), m. 239.5-40° (from C₆H₆). XIII on refluxing with pyridine gives 2′,6-dibromo-9-thia-3,4-benzofluorene 9,9-dioxide (XIV), m. 354-5° (from C₆H₆). XIV is reduced with LiAlH₄ to 9-thia-3,4-benzofluorene (XV). α-Naphthyl o-nitrophenyl sulfide, m. 152-3°, with H₂O₂ in HOAc yields α-naphthyl o-nitrophenyl sulfone (XVI), m. 128-9° (from EtOH). The isomeric β-naphthyl sulfone (XVII), m. 143.5-4°, is similarly prepared XVI in EtOH with Zn and HCl is reduced to o-aminophenyl α-naphthyl sulfone (XVIII), m. 177-8° (from EtOH). Similarly, XVII is reduced to o-aminophenyl β-naphthyl sulfone (XIX), m. 136-6.5°. Diazotization of XVIII and treatment with Cu gives II. Similar treatment of XIX followed by reduction with LiAlH₄ yields VII. o-Aminophenyl Ph sulfone with excess NaNO₂-HCl gives o-chlorophenyl Ph sulfone, m. 105-5.5°. Cyclization of o-PhC₆H₄SO₂Cl (XX) with AlCl₃ yields dibenzothiophene 5,5-dioxide, m. 229-30°. K o-α-naphthylbenzenesulfonate with PCl₅ gives o-α-naphthylbenzenesulfonyl chloride (XXI), m. 136-6.5° (from C₆H₆). XXI with AlCl₃ cyclized to VII. XX is treated with aqueous Na₂S to give o-PhC₆H₄SO₂H (XXII), m. 70-126°. XXII with SOCl₂ yields an oily sulfinyl chloride which is cyclized by AlCl₃ to dibenzothiophene 5-oxide, m. 189.5-90°. o-α-Naphthylbenzenesulfinyl chloride with AlCl₃ gives 9-thia-3,4-benzofluorene 9-oxide (XXIII), m. 147-8° (from C₆H₆-petr. ether). XXIII with SnCl₂ yields XV. XXIII is oxidized by H₂O₂ in HOAc to VII. 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 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, and sertaconazole, and also BTCP.COA of Formula: C8H4Br2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Design of reversible multi-electron redox systems using benzochalcogenophenes containing aryl and/or ferrocenyl fragments was written by Ogawa, Satoshi;Muraoka, Hiroki;Kikuta, Kenji;Saito, Fumihito;Sato, Ryu. And the article was included in Journal of Organometallic Chemistry in 2007.Synthetic Route of C8H4Br2S This article mentions the following:

2,3-Disubstituted benzo[b]thiophenes, 1,3-disubstituted benzo[c]thiophenes, and 1,3-disubstituted benzo[c]selenophene were systematically and selectively synthesized from benzo[b]thiophene or phthaloyl dichloride as a starting material, resp. Characterization of the mols. was performed by phys. and spectroscopic means and x-ray crystallog. analyses. The cyclic voltammograms of the chalcogenophene derivatives containing aryl fragments showed well-defined reversible both anodic and cathodic steps derived from the unusually stable 5π chalcogenophene radical cations and 7π chalcogenophene radical anions. The cyclic voltammograms of the novel chalcogenophene derivatives containing ferrocenyl fragments showed a well-defined reversible cathodic step derived from the unusually stable 7π chalcogenophene radical anions and 2 distinct reversible anodic steps derived from ferrocenium cations separated from each other by a thiophene-heterocycle. The radical character of several novel 7π chalcogenophene radical anions was measured by ESR spectroscopy. 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. Benzothiophene is relatively a stable molecule. 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 C8H4Br2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Ladder-Type P,S-Bridged trans-Stilbenes was written by Weymiens, Wannes;Zaal, Mark;Slootweg, J. Chris;Ehlers, Andreas W.;Lammertsma, Koop. And the article was included in Inorganic Chemistry in 2011.Electric Literature of C8H4Br2S This article mentions the following:

Phosphole-containing π-systems have emerged as building blocks with enormous potential as electronic materials because of the tunability of the phosphorus center. Among these, asym. P-bridged trans-stilbenes are still rare, and here an elegant and efficient synthesis toward such fluorescent mol. frameworks is described. Fine-tuning of the photophys. properties is attempted by enforcing the planarization of the phosphorus tripod and thus increasing the interaction between the phosphorus lone pair and the π-system. The electronic structure of the π-conjugated frameworks is analyzed with NMR, UV-vis and fluorescence spectroscopy, and time-dependent d. functional theory (TD-DFT) calculations 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. 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, and sertaconazole, and also BTCP.Electric Literature of C8H4Br2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Sensitive Assays by Nucleophile-Induced Rearrangement of Photoactivated Diarylethenes was written by Fredrich, Sebastian;Bonasera, Aurelio;Valderrey, Virginia;Hecht, Stefan. And the article was included in Journal of the American Chemical Society in 2018.Synthetic Route of C8H4Br2S This article mentions the following:

Upon light-induced isomerization, diarylethenes (DAEs) equipped with reactive aldehyde moieties rearrange selectively in the presence of amines, accompanied by decoloration. In a comprehensive study, the probe structure was optimized with regard to its inherent reactivity in the nucleophile-triggered rearrangement reaction. Detailed structure-reactivity relationships could be derived, in particular with regard to the type of integrated (het)aryl moieties as well as the location of the formyl residue, and the probes’ intrinsic reactivity with primary and secondary amines was optimized. Utilizing an ancillary base, the initially formed rearrangement product can engage in a subsequent catalytic cycle, leading to an amplified decoloration process. This addnl. catalytic pathway allows us to enhance the sensitivity of our method and successfully discriminate between amines and thiols. Moreover, probes that exhibit strong analyte-induced fluorescence modulation have been designed to further decrease the detection limit by using a more sensitive read-out. The optimized DAE probes are promising mol. components for future programmable sensing materials and devices. 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. Benzothiophene scaffolds are of great importance due to its increased presence in bioactive molecules. The different substitution patterns in these heterocycles offer new opportunities for drug discovery and other applications in materials science.Synthetic Route of C8H4Br2S

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis of novel benzo[b]furans and benzo[b]thiophenes: analogs of combretastatin and resveratrol was written by Chauhan, Jay;Monteil, Alexandre R.;Patterson, Steven E.. And the article was included in Heterocyclic Communications in 2010.HPLC of Formula: 6287-82-7 This article mentions the following:

A rapid and efficient synthesis of fused polyphenolic/polymethoxy benzofurans and benzothiophenes that have potential as antitumor agents and components of anti-HIV combination therapy was achieved. In the experiment, the researchers used many compounds, for example, 2,3-Dibromobenzo[b]thiophene (cas: 6287-82-7HPLC of Formula: 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. Due to its aromaticity, thiophenes do not exhibit the same properties as conventional thioethers.HPLC of Formula: 6287-82-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem