Day: February 9, 2023

A highly efficient one-pot reaction of 2-(gem-dibromovinyl)phenols(thiophenols) with K₄Fe(CN)₆ to 2-cyanobenzofurans(thiophenes) was written by Zhou, Wei;Chen, Wei;Wang, Lei. And the article was included in Organic & Biomolecular Chemistry in 2012.HPLC of Formula: 55219-11-9 This article mentions the following:

2-Cyanobenzofurans and 2-cyanobenzothiophenes I [R = H, 5-Me, 5-tBu, etc.; X = O, S] were prepared through an efficient one-pot Ullmann-reaction/cyanation reaction. In the presence of CuI/Na₂CO₃-Pd(OAc)₂/PPh₃ in DMF, the reaction of 2-(gem-dibromovinyl)phenols and 2-(gem-dibromovinyl)thiophenols with K₄Fe(CN)₆, as nontoxic and user-friendly cyanating reagent, proceeded smoothly to generate the corresponding 2-cyanobenzofurans and 2-cyanobenzothiophenes in good yields. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9HPLC of Formula: 55219-11-9).

Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9) 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.HPLC of Formula: 55219-11-9

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis of thiophenes and thiapyrans. III. Hydroxythianaphthenes and alkoxythianaphthenes was written by Sunthankar, A. V.;Tilak, B. D.. And the article was included in Proceedings – Indian Academy of Sciences, Section A in 1951.Formula: C9H8OS This article mentions the following:

Monomethoxythianaphthalenes are prepared by condensing a mercaptoanisole with BrCH₂CH(OMe)₂ (I) and effecting a ring closure of the resulting sulfide. p-MeOC₆H₄SH (7.6 g.), 1.2 g. Na, 1.25 g. NaI, 9.3 g. I, and 25 cc. absolute alc. boiled 2 h., and the crude product distilled yields 70% p-methoxyphenyl 2,2-dimethoxyethyl sulfide (II), b_2.5-3 155-60°; dinitrophenylhydrazone, m. 106-7°. From 6.1 g. II added to 30 g. P₂O₅ and 10 cc. H₃PO₄ at 150-60°/0.34 mm. is obtained 5-methoxythianaphthene (isolated as the picrate), which after distillation forms a white solid, m. 42-3°, b_0.52 85-90°; the yield is poor. Similarly prepared were m-methoxyphenyl 2,2-dimethoxyethyl sulfide, b_2.5 125-30° (2,4-dinitrophenylhydrazone, m. 123-4°); 6-methoxythianaphthene, b₁₆ 153-6° (62% yield)(picrate, m. 105-6°); o-methoxyphenyl 2,2-dimethoxyethyl sulfide, b₁₅ 175-80° (2,4-dinitrophenylhydrazone, m. 135-6°); 7-methoxythianaphthene, (III), b₁₅ 140-5° (yield 18%)(picrate, m. 110-11°); p-ethoxyphenyl 2,2-dimethoxyethyl sulfide, b₁₂ 180° (2,4-dinitrophenylhydrazone, m. 84-5°); 5-ethoxythianaphthene, b₁₂ 145° (picrate, m. 93°); 3-methoxy-p-toluenethiol, b₁₂ 130°; 3-methoxy-4-methylphenyl 2,2-dimethoxyethyl sulfide, b₁₅ 185° (2,4-dinitrophenylhydrazone, m. 123-4°); 6-methoxy-5-methylthianaphthene (IV), m. 62-3°, b₁₂ 160° (picrate, m. 107-8°); 6-methoxy-5-methylthianaphthene 1,1-dioxide (from 0.45 g. IV, 7 cc. glacial AcOH, and 3 cc. H₂O₂ heated 6 h. at 85°), m. 187°. Demethylation of 0.62 g. III with 5 g. pyridine-HCl by heating 9 h. at 180° gave 0.5 g. (88%) 7-hydroxythianaphthene, b₈ 135°, m. 67-8° (picrate, m. 184-6°); from IV by the same procedure is obtained 6-hydroxy-5-methylthianaphthene, m. 146-7°, b₁₀ 160-5°. All b.ps. are given as bath temperature 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. Benzothiophenes are valuable heterocycles that are widely used in medicines, agrochemicals, and materials science. 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

Preparation of polyfunctional nitriles by the cyanation of functionalized organozinc halides with p-toluenesulfonyl cyanide was written by Klement, Ingo;Lennick, Klaus;Tucker, Charles E.;Knochel, Paul. And the article was included in Tetrahedron Letters in 1993.Quality Control of Benzo[b]thiophene-2-carbonitrile This article mentions the following:

Various alkyl, alkenyl, alkynyl, benzylic, aromatic or heterocyclic organozinc halides bearing functional groups such as an ester, a boronic ester, a cyanide, a halide or a trialkoxysilyl group react under mild conditions with p-toluenesulfonyl cyanide (TosCN) affording polyfunctional nitriles in 69-93% yields. Thus, (E)-Cl(CH₂)₃CH:CHZnI was treated sequentially with BuLi, ZnI₂, and TosCN in THF to give 72% (E)-Cl(CH₂)₃CH:CHCN. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9Quality Control of Benzo[b]thiophene-2-carbonitrile).

Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9) 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 is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, and sertaconazole, and also BTCP.Quality Control of Benzo[b]thiophene-2-carbonitrile

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Synthesis and properties of a new photochromic diarylethene 1-(2-methylbenzothiophene-3-yl)-2-[2-methy-5-(4-methoxyl-3-formyl) phenyl-3-thienyl] perfluorocyclopentene was written by Feng, Yuchuan;Li, Jie. And the article was included in Advanced Materials Research (Durnten-Zurich, Switzerland) in 2014.Recommanded Product: 3-Bromo-2-methylbenzo[b]thiophene This article mentions the following:

A novel photochromic diarylethene 1-(2-methylbenzothiophene-3-yl)-2- [2-methy-5-(4-methoxyl-3-formyl)phenyl-3-thienyl] perfluorocyclopentene has been synthesized. Its properties, including photochromic behavior and fluorescent features, have been investigated in detail. This diarylethene showed good photochromism both in solution and PMMA film and exhibited good fluorescence switching. Its also exhibits optical record property. In the experiment, the researchers used many compounds, for example, 3-Bromo-2-methylbenzo[b]thiophene (cas: 10243-15-9Recommanded Product: 3-Bromo-2-methylbenzo[b]thiophene).

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

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

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

Photochemical cycloadditions of 2,3-dihalobenzo[b]thiophenes: stereochemical and mechanistic results was written by Neckers, D. C.;Wagenaar, F. L.;Hauenstein, D.;Jacobson, R. A.. And the article was included in Journal of Organic Chemistry in 1983.Related Products of 6287-82-7 This article mentions the following:

Photocycloaddition of CH₂:CHBr (I) to II (R = Cl) with Ph₂CO as sensitizer and 2,6-di-tert-butyl-p-cresol as inhibitor gave 75% III (R¹ = Br, R² = H)/III (R¹ = H, R² = Br) as a 1:1 mixture With cis-ClCH:CHCl (cis–IV) instead of I, the reaction gave V (R³ = Cl, R⁴ = H); with trans–IV a 2nd product (V; R³ = H, R⁴ = Cl) was also obtained. The dehydrochlorination of V was described. The photoreaction of I with II (R = Br) gave only VI (R⁵ = CH₂CHBr₂); dehydrobromination of the side chain of this product was carried out. The photoreaction of cis–IV and C₂H₄ with I (R = Br) gave VI (R⁵ = CHClCHClBr, CH₂CH₂Br, resp.). X-ray analyses were described. 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 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.Related Products of 6287-82-7

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

The Baeyer-Villiger reaction of some acetylthianaphthene derivatives was written by Matsuki Yasuo;Fujieda, Kunimi. And the article was included in Nippon Kagaku Zasshi in 1967.COA of Formula: C8H4Br2S This article mentions the following:

3-Bromothianaphthene (82.7 g.) in 500 ml. CHCl3 treated with 64 g. Br in 50 ml. CHCl3 for 20 hrs. gave 110.3 g. 2,3-dibromothianaphthene (I). Bromination of thianaphthene yielded 86.2% I. Oxidation of I with H2O2 in AcOHAc2O gave 90% I 1,1-dioxide, m. 156-7°. Similarly 6-acetyl-2,3-dibromothianaphthene 1,1-dioxide (II), m. 187-7.5°, and 6-acetyl-3-bromothianaphthene 1,1-dioxide (III), m. 176-6.5°, were prepared 6-Acetyl-2,3-dibromothianaphthene (IV) (6.6 g.) treated with 0.036 mole F3CCO2H (V) and 0.03 mole H2O2 gave 3.2 g. recovered IV, 0.1 g. 6-acetoxy-2,3-dibromothianaphthene, m. 193-4°, and 2.0 g. II. Similarly 6-acetyl-3-bromothianaphthene (VI) gave 98% III. Treating 1 mole IV with 5 moles F3CCO2OH yielded a 4:1 mixture of II and 6-acetoxy-2,3-dibromothianaphthene 1,1-dioxide, of which hydrolysis gave 2,3-dibromo-6-hydroxythianaphthene 1,1-dioxide, m. 280°. Similarly VI gave a 4:5 mixture of III and 6-acetoxy-3-bromothianaphthene 1,1-dioxide, of which hydrolyis yielded 6-hydroxythianaphthene 1,1-dioxide (VII), m. 228-8.5°. The mechanism of formation of VII is discussed. Oxidation of 2.5 g. VI with 1.3 g. SeO2 in aqueous dioxane yielded 3-bromo-6-thianaphthenylglyoxal, m. 254-5°; quinoxaline derivative m. >300°. Treating VI with 1.28 g. NaN3 5 ml. HOAc, and 0.5 g. concentrated H2SO4 yielded 88.6% 6-acetamido-3-bromothianaphthene, m. 145-6°, and 8% 6-amino-3-bromothianaphthene sulfate, m. 240-5° (decomposition). 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. 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

A General and Convenient Catalytic Synthesis of Nitriles from Amides and Silanes was written by Zhou, Shaolin;Junge, Kathrin;Addis, Daniele;Das, Shoubhik;Beller, Matthias. And the article was included in Organic Letters in 2009.Recommanded Product: 55219-11-9 This article mentions the following:

A new and convenient protocol for the catalytic dehydration of aromatic and aliphatic amides using silanes in the presence of catalytic amounts of fluoride is presented. The synthesis of aliphatic and aromatic nitriles proceeds with high selectivity under mild conditions. Notably, a wide substrate range is converted in good to excellent yields. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9Recommanded Product: 55219-11-9).

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

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

Iron(II)-Catalyzed Direct Cyanation of Arenes with Aryl(cyano)iodonium Triflates was written by Shu, Zhibin;Ji, Wenzhi;Wang, Xi;Zhou, Yujing;Zhang, Yan;Wang, Jianbo. And the article was included in Angewandte Chemie, International Edition in 2014.Application In Synthesis of Benzo[b]thiophene-2-carbonitrile This article mentions the following:

A direct oxidative cyanation of arenes under iron [Fe(II)] catalysis with [3,5-bis(trifluoromethyl)phenyl](cyano)iodonium triflate (DFCT) as the cyanation agent has been developed. The reaction is applicable to wide range of aromatic substrates, including polycyclic structures and heteroaromatic compounds Under optimized conditions the synthesis of the target compounds was achieved using acetic acid iron(2+) salt (2:1) [iron(II) acetate] as catalyst and cyano[4-(trifluoromethyl)phenyl]iodonium trifluoromethanesulfonate (1:1) as cyano group source. Starting materials included 1,4-dimethylbenzene (alkyl arene), naphthalene, anthracene, phenanthrene, 1-[tris(1-methylethyl)silyl]-1H-pyrrole, 1-[(4-methylphenyl)sulfonyl]-1H-pyrrole, benzo[b]thiophene, benzofuran, 1-(3-methyl-1H-indol-1-yl)-ethanone (indole derivative),. The title compounds thus formed included aromatic nitriles, such as benzonitrile derivatives, 9-anthracenecarbonitrile, 1-naphthalenecarbonitrile, 1-[(4-methylphenyl)sulfonyl]-1H-pyrrole-2-carbonitrile, 9-phenanthrenecarbonitrile, benzo[b]thiophene-2-carbonitrile, etc. In the experiment, the researchers used many compounds, for example, Benzo[b]thiophene-2-carbonitrile (cas: 55219-11-9Application In Synthesis of Benzo[b]thiophene-2-carbonitrile).

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 is found within the chemical structures of pharmaceutical drugs such as raloxifene, zileuton, and sertaconazole, and also BTCP.Application In Synthesis of Benzo[b]thiophene-2-carbonitrile

Referemce:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem