4565-32-6

Usage

Class of organic compounds

benzo[b]thiophenes

Physical state

colorless to light yellow liquid

Uses

building block in the synthesis of pharmaceuticals, agrochemicals, organic electronic materials, and dyes

Environmental concern

potential contaminant

Health hazards

known irritant to the eyes, skin, and respiratory system, requires proper handling and safety procedures.

InChI:InChI=1/C8H8S/c1-2-4-8-7(3-1)5-6-9-8/h1-4H,5-6H2

Upstream product

• 95-15-8 Benzo[b]thiophene 
• 5394-13-8 2-bromo-1-benzothiophene 
• 1645-69-8 2,2,3,3-tetrafluoro-2,3-dihydrobenzothiophene 
• 82135-95-3 1-methylthiaindan hexafluorophosphate 
• 95-47-6 o-xylene 
• 177748-68-4 2-Allyloxy-thiobenzoic acid S-[2-(2-iodo-phenyl)-ethyl] ester 
• 177748-55-9 ((E)-3-Phenyl-allyloxy)-thioacetic acid S-[2-(2-iodo-phenyl)-ethyl] ester 
• 67-56-1 methanol 
• 31366-25-3 tetrathiafulvalene 
• 24850-33-7 allyltributylstanane 
• 461383-63-1 S-(2-iodophenethyl) 2-(azidomethyl)benzenecarbothioate 
• 76-63-1 allytriphenyltin 
• 461383-65-3 S-(2-iodophenethyl) 4-azidobutanethioate 
• 461383-66-4 S-(2-iodophenethyl) 4-azido-4-phenylbutanethioate 

Downstream Products

• 4500-58-7 2-ethylthiophenol 
• 100-41-4 ethylbenzene 
• 95-15-8 Benzo[b]thiophene 
• 26524-83-4 racemic 2,3-dihydrobenzo[b]thiophene-1-oxide 
• 135162-32-2 trans-dichlorobis(2,3-dihydrobenzo{b}thiophene)palladium(II) 
• 227005-28-9 CH₃C[CH₂P(C₆H₅)2]3IrH₂(C₈SH₈)⁽¹⁺⁾*B(C₆H₅)4^(1-)=CH₃C[CH₂P(C₆H₅)2]3IrH₂(C₈SH₈)B(C₆H₅)4 
• 93669-99-9 ethyl 7-benzoyl-5-chloro-2,3-dihydro-1,1-dioxobenzothiophene-3-carboxylate 
• 97483-28-8 7-(4-chlorobenzoyl)-2,3-dihydrobenzothiophene-5-ylacetic acid 
• 97483-27-7 [7-(4-Chloro-benzoyl)-benzo[b]thiophen-5-yl]-acetic acid 
• 104172-31-8 (7-Benzoyl-2,3-dihydro-benzo[b]thiophen-5-yl)-acetic acid 
• 104172-32-9 (7-Benzoyl-benzo[b]thiophen-5-yl)-acetic acid 

Relevant academic research and scientific papers

Stereochemistry of Intramolecular Homolytic Substitution at the Sulphur Atom of a Chiral Sulphoxide

The formation of the cyclic sulphoxide (R)-(6) by treatment of the bromoarene (R)-(2) with tributylstannane indicates that intramolecular homolytic substitution at the sulphur centre of the sulphoxide group proceeds with strict inversion of configuration.

Highly efficient one-pot multi-directional selective hydrogenation and N-alkylation catalyzed by Ru/LDH under mild conditions

Atomic economy, non-toxicity, harmlessness and multidirectional selectivity advocated by green chemistry have increasingly become a hot and difficult research topic. Herein, we present a highly efficient, one-pot tandem and easy-to-operate method through which we could directly produce a broad range of multi-directional selective hydrogenated amines or N-alkyl aliphatic amines using aromatic nitro compounds as raw materials. Ru/LDH with characteristics of layered mesoporous structure, well dispersed small Ru nanoparticles and LDH stabilization to the Ru NPs was employed as the catalyst. It is remarkable that multi-directional superb chemoselectivity to aromatic amines, alicyclic amines as well as N-alkyl aliphatic amines could be achieved with excellent catalytic activity and recyclability by tuning reaction conditions over 5wt%Ru/LDH-2. Additionally, this catalytic system also exhibited attractive activity and multi-directional chemoselectivity in the hydrogenation of quinoline and its derivatives with solvents of different polarity. Chemoselectivity to 5,6,7,8-tetrahydroquinoline derivatives could reach as high as 95.6 %.

Competitive adsorptions between thiophenic compounds over a CoMoS/Al2O3 catalyst under deep HDS of FCC gasoline

The transformation of various model sulfur compounds (2-methylthiophene: 2MT, 3-methylthiophene: 3MT and benzothiophene: BT) representative of sulfur compounds in FCC gasoline was investigated over a CoMoS/Al2O3 catalyst. More specifically, a quantitative reactivity scale was established with BT being more reactive than 3MT and 2MT. In mixture, their reactivity was reduced due to the presence of the other sulfur compound, the scale of reactivity being preserved. BT strongly inhibits the transformation of 2MT. With a single kinetic model based on a Langmuir Hinshelwood formalism, kinetic and adsorption parameters were calculated and the results explained by mutual competitive adsorption between 2MT and BT with a higher adsorption constant for BT compared to that of 2MT.

Rh(CAAC)-Catalyzed Arene Hydrogenation: Evidence for Nanocatalysis and Sterically Controlled Site-Selective Hydrogenation

We report the arene hydrogenation of ethers, amides, and esters at room temperature and low hydrogen pressure, starting from [(CAAC)Rh(COD)Cl] (CAAC = cyclic alkyl amino carbene). Kinetic, mechanistic, and Rh K-edge XAFS studies showed formation of Rh nanoparticles from [(CAAC)Rh(COD)Cl], in contrast to a previous report of [(CAAC)Rh(COD)Cl] functioning as a homogeneous catalyst for arene hydrogenation. We determined that the site-selective arene hydrogenation catalyzed by this system is under steric control, as shown by detailed competition experiments with derivatives of ethers, amides, and esters bearing different aromatic rings of varying electronic and steric influence. This work illustrates the potential of CAAC ligands in the formation and stabilization of a colloidal dispersion of stable nanoparticle catalysts.

NiMo catalysts supported on the Nb modified mesoporous SBA-15 and HMS: Effect of thioglycolic acid addition on HDS

Nb modified mesoporous SBA-15 and HMS materials were synthesized and studied as a support of NiMo. Calcined co-impregnated NiMo catalysts were prepared using ammonium heptamolybdate and nickel nitrate. Moreover, NiMo catalysts prepared in this manner were treated with thioglycolic acid (TGA). For comparison, NiMo catalysts were prepared by a simultaneous impregnation of the supports with Ni, Mo precursors and TGA. The TGA:Mo molar ratio was 4.0. The supports and NiMo catalysts were characterized by N2 physisorption, small- and wide-angle XRD, TPD-NH3, SEM, UV-vis DRS, FTIR and XPS. Catalyst activity was examined in hydrodesulfurization (HDS) reactions of 1-benzothiophene and thiophene at 350°C. It was found that simultaneous impregnation by Ni, Mo and TGA led to higher HDS activities than the sequential treatment of the calcined NiMo catalysts by TGA.

Intramolecular Cyclization of Acyl Radicals onto the Azido Group: A New Radical Approach to Cyclized Lactams

(Equation Presented) Reagents: i, Bu3SnH/AlBN; ii, (TMS)3SiH/AlBN. Aryl- and alkyl-derived azidoacyl radicals, generated from thiolesters by intramolecular homolytic substitution at the sulfur, can undergo five- and six-membered cyclization onto the azido moiety to give cyclized lactams.

The effect of the base in the fragmentation of nucleotide C4′ radicals

A series of 3′-O-diethylphosphoryl-4′-α-[(2-halophenylethylthio) carbonyl] substituted esters of thymidine, cytidine, adenosine and guanosine are prepared by total synthesis and used as C4′-radical precursors in a competition kinetic method using tributyltin hydride as the reductant. The pseudo-first order rate constants for the C4′-radicals so generated decrease in the order guansoine>cytidine>adenosine>thymidine with that for guanosine being too rapid for determination by the present competition kinetic method. A 119Sn NMR method is presented for estimation of the purity of tin hydride solutions.

The role of neighbouring group participation in TTF-mediated 'radical- polar crossover' reactions: Trapping of aliphatic radicals by TTF+.

Trapping of secondary alkyl radicals with tetrathiafulvalenium tetrafluoroborate (TTF+.BF4-) leads to S-alkyltetrathiafulvalenium tetrafluoroborate salts; the solvolysis of such salts is critically dependent on the presence of appropriately sited neighbouring groups.

Ruthenium carbonyls as benzo[b]thiophene hydrodesulfurization catalysts in homogeneous phase

The catalytic activity of mononuclear and polynuclear ruthenium complexes in the benzo[b]thiophene (BT) hydrodesulfurization (HDS) has been tested in the temperature range between 150 and 170°C under 100 bar of hydrogen. The ruthenium complexes tested are shown to be catalytically active in the hydrogenation of BT to 2,3-dihydrobenzo[b]thiophene (DHBT) and 2-ethylthiophenol. The best performance was provided by H4Ru4(CO)8(PPh3)4 when working at 170°C: In these conditions BT is hydrogenated to DHBT with a conversion of 38.2% after 96 h or 81.2% after 384 h. Ethylbenzene (conversion 4.9%) is also formed confirming that a complete HDS of the substrate (even if in a low amount) may be obtained. The addition of a strong base (tBuOK) as a co-catalyst changes the chemioselectivity of the reaction. The mononuclear complexes are less active than the cluster ones. BT is in fact converted to DHBT up to 19.5% in the presence of Ru(CO)3(PPh3)2 under the same conditions. These data show that this reaction is promoted by the cooperation of several metal atoms in the catalytic intermediates.

Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 12. Extrusion of Ph3P from sulfonyl ylides and reactivity of the resulting sulfonyl carbenes

Twelve sulfonyl stabilised phosphorus ylides have been prepared and their behaviour upon flash vacuum pyrolysis at 600°C has been examined. Examples with an arylsulfonyl substituent undergo loss of Ph3PO to give intractable products but those with an arylmethylsulfonyl substituent separately lose Ph3P and SO2 to give products consistent with the intermediacy of sulfonyl carbenes. X-Ray structure determinations of one ylide from each series show a more significant P-O non-bonding interaction in the first case, providing some explanation for the different thermal reactivity.