20532-30-3

Usage

Uses

Used in Pharmaceutical Industry:
5-Methoxy-1-benzothiophene serves as an intermediate in the synthesis of pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its unique chemical structure allows for the creation of diverse medicinal compounds with potential applications in treating various diseases and conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Methoxy-1-benzothiophene is utilized as an intermediate in the production of agrochemicals, such as pesticides and herbicides. Its incorporation into these products can enhance their effectiveness in protecting crops and managing pests, thereby contributing to increased agricultural productivity.
Used in Organic Synthesis:
5-Methoxy-1-benzothiophene is employed as a building block in organic synthesis, enabling the preparation of various functional materials and organic compounds. Its versatile chemical structure allows for the synthesis of a wide range of molecules with different properties and applications, making it a valuable component in the development of new materials and compounds.
Used in Production of Fine Chemicals:
As an important chemical in the field of organic chemistry, 5-Methoxy-1-benzothiophene is used in the production of fine chemicals. These specialty chemicals are utilized in various industries, including pharmaceuticals, fragrances, and flavorings, where their unique properties and reactivity are essential for creating high-quality products.

InChI:InChI=1/C9H8OS/c1-10-8-2-3-9-7(6-8)4-5-11-9/h2-6H,1H3

Upstream product

• 19301-35-0 benzo[b]thiophen-5-ol 
• 77-78-1 dimethyl sulfate 
• 858816-12-3 (4-methoxy-phenylsulfanyl)-acetaldehyde dimethylacetal 
• 67-56-1 methanol 
• 4923-87-9 5-bromobenzo[b]thiophene 
• 183997-18-4 5-Methoxy-2,3-dihydrobenzothiophene 
• 91906-21-7 4-methoxythiophenoxylacetaldehyde dimethyl acetal 
• 74-88-4 methyl iodide 
• 72002-19-8 2,3-dihydro-5-methoxybenzo[b]thiophen-3-one 
• 121424-95-1 N,N-diethyl-3-methoxy-6-(methylthio)-2-(trimethylsilyl)benzamide 
• 95094-87-4 5-hydroxy benzo[b]thiophene-2-carboxylic acid 
• 5020-41-7 2-(3-methoxyphenyl)-ethanol 
• 183997-13-9 Benzyl 2-(3-methoxyphenyl)ethyl sulfide 
• 20532-28-9 5-aminobenzo[b]thiophene 

Downstream Products

• 80824-40-4 5-methoxy-3-phenyl-2,3-dihydrobenzothiophen 
• 193965-31-0 5-methoxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophene 
• 19301-35-0 benzo[b]thiophen-5-ol 
• 53299-66-4 5-methoxy-2-methylbenzo[b]thiophene 
• 193965-30-9 5-methoxybenzo[b]thiophen-2-yl-2-boronic acid 
• 1373162-73-2 (R)-N-(3-(benzo[b]thiophen-5-yloxy)-2-hydroxypropyl)-N-isobutyl-3,4-dimethoxybenzene sulfonamide 
• 35134-07-7 3-methoxy-2-thiophenecarboxaldehyde 
• 98316-32-6 4-methoxy-thiophene-2-carboxaldehyde 
• 19492-99-0 methyl 5-methoxylbenzo[b]thiophene-2-carboxylate 
• 1402598-40-6 N-((5-methoxy-1-benzothiophen-2-yl)(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide 
• 1402598-45-1 N-((5-hydroxy-1-benzothiophen-2-yl)(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide 
• 1402599-43-2 N-((5-(benzyloxy)-1-benzothiophen-2-yl)(phenyl)methyl)-3,4-dihydro-2H-1,5-benzodioxepine-7-sulfonamide 
• 641633-30-9 C₆₉H₆₈F₆N₂O₄S₂ 

Relevant academic research and scientific papers

5-Substituted Benzothiophenes: Synthesis, Mechanism, and Kinetic Studies

The kinetics of the reaction of 4-methoxythiophenoxyacetaldehyde diethyl acetal, 4-nitrothiophenoxyacetaldehyde diethyl acetal, and 3-methoxythiophenoxyacetaldehyde diethyl acetal in polyphosphoric acid has been explained. The kinetic behavior has been ex

Enantioselective hydroarylation or hydroalkenylation of benzo[b]thiophene 1,1-dioxides with organoboranes

An efficient protocol for the asymmetric hydroarylation and hydroalkenylation of benzo[b]thiophene 1,1-dioxides with organoboranes has been developed. The combination of a rhodium(I) precatalyst and a chiral diene ligand constitutes the catalytic system, which enables the facile synthesis of 2,3-dihydrobenzo[b]thiophene 1,1-dioxides in good yields with high enantioselectivities. The merging of this asymmetric hydroarylation with the downstream alkylations delivers 2,3-dihydrobenzo[b]thiophene 1,1-dioxides that contain two continuous quaternary stereocenters with high enantioselectivities in a diastereodivergent manner.

Aryl or heteroaryl methoxylation reaction method

The invention discloses an aryl or heteroaryl methoxylation reaction method. The method comprises the following steps: preparing a substrate. The coupling agent, ligand, solvent, catalyst and base are mixed homogeneously in an inert gas to give the aryl or heteroaryl methoxy compounds. Compared with a methoxylation reaction method in the prior art, the method has the advantages that the reaction system conditions are mild, the usage amount of the catalyst and the ligand is low to 5% of the amount of the substrate material, and the catalytic efficiency is improved. The method has better compatibility to different substrate expansion and discovery of aryl halides or heteroaryl halides with different functional groups. The yield of aryl or heteroaryl methoxy compounds prepared by the method disclosed by the invention is 36% - 89%.

Copper-Catalyzed Methoxylation of Aryl Bromides with 9-BBN-OMe

A Cu-catalyzed cross-coupling reaction between aryl bromides and 9-BBN-OMe to provide aryl methyl ethers under mild conditions is reported. The oxalamide ligand BHMPO plays a key role in the transformation. Various functional groups on bromobenzenes are well tolerated, providing the desired anisole products in moderate to high yields.

New heteroaryl carbamates: Synthesis and biological screening in vitro and in mammalian cells of wild-type and mutant HIV-protease inhibitors

New heteroaryl HIV-protease inhibitors bearing a carbamoyl spacer were synthesized in few steps and high yield, from commercially available homochiral epoxides. Different substitution patterns were introduced onto a given isopropanoyl-sulfonamide core that can have either H or benzyl group. The in vitro inhibition activity against recombinant protease showed a general beneficial effect of both carbamoyl moiety and the benzyl group, ranging the IC50 values between 11 and 0.6 nM. In particular, benzofuryl and indolyl derivatives showed IC50 values among the best for such structurally simple inhibitors. Docking analysis allowed to identify the favorable situation of such derivatives in terms of number of interactions in the active site, supporting the experimental results. The inhibition activity was also confirmed in HEK293 mammalian cells and was maintained against protease mutants. Furthermore, the metabolic stability was comparable with that of the commercially available inhibitors.

C-benzo five-membered heteroaromatic aryl glucoside derivative as well as preparation method and application thereof

The invention discloses a C-benzo five-membered heteroaromatic aryl glucoside derivative shown in the general formula (I) (in the description), a preparation method of the derivative or an intermediate of the derivative, as well as application of the derivative. In the general formula (I), R, R1, R2, R3, R4, X and Y are defined in the description. The C-benzo five-membered heteroaromatic aryl glucoside derivative is novel in structure, has quite strong inhibitory activity on SGLT-2, has high selection ratio for SGLT-1 and SGLT-2, and can be used for preparing drugs for treating and preventing diseases relevant to SGLT-2.

Mild and general palladium-catalyzed synthesis of methyl aryl ethers enabled by the use of a palladacycle precatalyst

A general method for the Pd-catalyzed coupling of methanol with (hetero)aryl halides is described. The reactions proceed under mild conditions with a wide range of aryl and heteroaryl halides to give methyl aryl ethers in high yield.

Completely regioselective direct C-H functionalization of benzo[b]thiophenes using a simple heterogeneous catalyst

The first completely selective C3 C-H arylation of benzo[b]thiophenes is reported, demonstrating previously unexploited reactivity of palladium. Benzo[b]thiophenes are coupled with readily available aryl chlorides using a ligand-free, dual catalytic system of heterogeneous Pd/C and CuCl. The reaction is operationally simple and insensitive to air and moisture, and it provides valuable products with complete selectivity. Significant investigations into the nature of the active catalytic species and mechanistic considerations are discussed.

Synthesis and biological evaluation of novel small non-peptidic HIV-1 PIs: The benzothiophene ring as an effective moiety

Synthesis and biological evaluation of a new series of potential HIV-1 protease inhibitors incorporating different heterocycles are described. The variation of heteroatom in such molecules has displayed totally different biological activities and a benzothiophene containing inhibitor has shown high potency against wild type HIV-1 protease with IC50 = 60 nM, thanks to the lower desolvation penalty to be payed by such hydrophobic moiety.

Antitumor agents. 284. new desmosdumotin B analogues with bicyclic B-ring as cytotoxic and antitubulin agents

We previously reported that the biological acti-vity of analogues of desmosdumotin B (1) was dramatically changed depending on the B-ring system. A naphthalene B-ring analogue 3 exerted potent in vitro activity against a diverse panel of human tumor cell lines with GI50 values of 0.8-2.1 μM. In contrast, 1 analogues with a phenyl B-ring showed unique selective activity against P-glycoprotein (P-gp) overexpressing multidrug resistant cell line. We have now prepared and evaluated 1 analogues with bicyclic or tricyclic aromatic B-ring systems as in vitro inhibitors of human cancer cell line proliferation. Among all synthesized derivatives, 21 with a benzo[b]thiophenyl B-ring was highly active, with GI50 values of 0.06-0.16 μM, and this activity was not influenced by overexpression of P-gp. Furthermore, 21 inhibited tubulin assembly in vitro with an IC50 value of 2.0 μM and colchicine binding by 78% as well as cellular microtubule polymerization and spindle formation.