75998-29-7

Usage

Uses

Used in Pharmaceutical Industry:
3-CHLORO-6-METHOXYBENZO[B]THIOPHENE-2-CARBONYL CHLORIDE is used as a versatile building block for the preparation of pharmaceuticals. Its reactivity as a carbonyl chloride allows for the production of various functionalized benzo[b]thiophene derivatives, which can be further utilized in the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical industry, 3-CHLORO-6-METHOXYBENZO[B]THIOPHENE-2-CARBONYL CHLORIDE is used as a key intermediate in the synthesis of agrochemicals. Its ability to form various benzo[b]thiophene derivatives makes it a valuable component in the creation of effective and targeted agrochemical products.
Used in Fine Chemicals Industry:
3-CHLORO-6-METHOXYBENZO[B]THIOPHENE-2-CARBONYL CHLORIDE is also used in the fine chemicals industry as a precursor for the synthesis of heterocyclic compounds with potential biological activity. Its unique structure and reactivity contribute to the development of novel and specialized chemical products.
Used in Organic Synthesis:
As a carbonyl chloride derivative, 3-CHLORO-6-METHOXYBENZO[B]THIOPHENE-2-CARBONYL CHLORIDE is used in organic synthesis to create a wide range of chemical compounds. Its versatility and reactivity make it an essential component in the synthesis of various organic compounds for research and industrial applications.

InChI:InChI=1/C10H6Cl2O2S/c1-14-5-2-3-6-7(4-5)15-9(8(6)11)10(12)13/h2-4H,1H3

Upstream product

• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 5676-64-2 (Z)-3-(4-methoxyphenyl)acrylic acid 

Downstream Products

• 108144-49-6 3-Chloro-6-methoxy-N-(2-methoxyphenyl)benzothiophene-2-carboxamide 
• 1133421-22-3 benzyl 3-benzyloxy-6-methoxy-1-benzo[b]thiophene-2-carboxylate 
• 1281988-28-0 2-(4-chlorophenylamino)-2-oxoethyl 3-chloro-6-methoxybenzo[b]thiophene-2-carbothioate 
• 1281988-30-4 2-(4-methoxyphenylamino)-2-oxoethyl 3-chloro-6-methoxybenzo[b]thiophene-2-carbothioate 
• 1281988-32-6 2-(4-bromophenylamino)-2-oxoethyl 3-ehloro-6-methoxybenzo[b]thiophene-2-carbothioate 
• 34576-80-2 3,7-dichloro-6-methoxybenzothiophene-2-carbonyl chloride 
• 108144-50-9 3-Chloro-6-methoxy-N-(3-methoxyphenyl)benzothiophene-2-carboxamide 

Relevant academic research and scientific papers

Construction of 2,3-disubstituted benzo[: B] thieno[2,3- d] thiophenes and benzo[4,5]selenopheno[3,2- b] thiophenes using the Fiesselmann thiophene synthesis

A series of 3-(hetero)aryl-substituted benzo[b]thieno[2,3-d]thiophenes, bearing various electron withdrawing groups at C-2 position of their scaffolds, were obtained using a convenient approach based on the Fiesselmann thiophene synthesis. To realize this strategy, the Friedel-Crafts acylation of (hetero)arenes with easily accessible 3-chlorobenzo[b]thiophene-2-carbonyl chlorides was initially performed to afford 3-chloro-2-(hetero)aroylbenzo[b]thiophenes. The latter ketones were treated either with methyl thioglycolate in the presence of DBU and calcium oxide powder or successively with sodium sulfide, an alkylating agent, containing methylene active component, and also DBU and calcium oxide, to form the desired benzo[b]thieno[2,3-d]thiophene derivatives. In addition, similar benzo[4,5]selenopheno[3,2-b]thiophene derivatives were prepared in the same manner using 3-bromobenzo[b]selenophen-2-yl substrates. The obtained functional derivatives of both benzo[b]thieno[2,3-d]thiophene and benzo[4,5]selenopheno[3,2-b]thiophene are of interest for further elaboration of organic semiconductor materials.

Synthesis Development of the Selective Estrogen Receptor Degrader (SERD) LSZ102 from a Suzuki Coupling to a C-H Activation Strategy

The development of the synthetic process to the selective estrogen receptor degrader (SERD) drug candidate LSZ102 from the medicinal chemistry synthesis to the streamlined large-scale manufacturing route is described. The synthesis of LSZ102 could be sign

Design and Synthesis of Basic Selective Estrogen Receptor Degraders for Endocrine Therapy Resistant Breast Cancer

The clinical steroidal selective estrogen receptor (ER) degrader (SERD), fulvestrant, is effective in metastatic breast cancer, but limited by poor pharmacokinetics, prompting the development of orally bioavailable, nonsteroidal SERDs, currently in clinical trials. These trials address local breast cancer as well as peripheral metastases, but patients with brain metastases are generally excluded because of the lack of blood-brain barrier penetration. A novel family of benzothiophene SERDs with a basic amino side arm (B-SERDs) was synthesized. Proteasomal degradation of ERα was induced by B-SERDs that achieved the objectives of oral and brain bioavailability, while maintaining high affinity binding to ERα and both potency and efficacy comparable to fulvestrant in cell lines resistant to endocrine therapy or bearing ESR1 mutations. A novel 3-oxyazetidine side chain was designed, leading to 37d, a B-SERD that caused endocrine-resistant ER+ tumors to regress in a mouse orthotopic xenograft model.

Construction of Heteroacenes with Fused Thiophene and Pyrrole Rings via the Fischer Indolization Reaction

A convenient approach to ladder-type 6H-benzo[4′,5′]thieno[2′,3′:4,5]thieno[3,2-b]indoles bearing various substituents in both terminal benzene rings has been developed. The protocol suggested for preparing these N,S-heteroacenes is based on using easily

Synthesis, characterization and structure activity relationship studies of benzo[b]thiophene derivatives as promising class of antimicrobial agents

Here we employed simple chemistry for the synthesis of a new potent series of benzo[b]thiophene containing 2-carbonylchlorides (1), 2-isopropyl carboxamides (2), 2-(piperidin-1-yl)-methanones (3) by nucleophilic chloro cyclocondensation of substituted-cin

MODULATORS OF TLR3/DSRNA COMPLEX AND USES THEREOF

The present invention provides compounds and compositions that can modulate formation of Toll-like receptor 3 (TLR3) and double-stranded RNA (dsRNA) complex, and methods for using the same. In particular, some aspects of the invention provide compounds of the formula (I) compositions comprising and methods for using the same, where n, Ar1, Ar2, X1, X2, X3, Z1, and Z2 are those defined herein.

Small-molecule inhibitors of the TLR3/dsRNA complex

The protein-RNA interface has been regarded as "undruggable" despite its importance in many biological processes. The toll-like receptor 3 (TLR3)/double-stranded RNA (dsRNA) complex provides an exciting target for a number of infectious diseases and cancers. We describe the development of a series of small-molecule probes that were shown to be competitive inhibitors of dsRNA binding to TLR3 with high affinity and specificity. In a multitude of assays, compound 4a was profiled as a potent antagonist to TLR3 signaling and also repressed the expression of downstream signaling pathways mediated by the TLR3/dsRNA complex, including TNF-α and IL-1β.

Synthesis and cannabinoid activity of a variety of 2,3-substituted 1-benzo[b]thiophen derivatives and 2,3-substituted benzofuran: Novel agonists for the CB1 receptor

An exploratory chemical effort has been undertaken to develop a novel series of compounds as selective CB1 agonists. It is hoped that compounds of this type will have clinical utility in pain control and cerebral ischaemia following stroke or traumatic head injury. We report here medicinal chemistry studies directed towards the investigation of several classes of 1-benzo[b]thiophen and benzofuran derivatives as novel CB1 agonists. We have discovered a novel series of compounds, which contain a 1-benzo[b]thiophen or a benzofuran group as the central aromatic group. Our investigation of this series of compounds has enhanced our understanding of the importance of binding sites within the CB1 receptor for favourable CB1 potency. Our understanding of these factors allowed us to modify the structure of a 1-benzothiophen derivative and improve its potency at the CB1 receptor. CSIRO 2008.

Telomerase inhibitors

Methods and compositions for treating cancer and other diseases in which inhibition of telomerase activity can ameliorate disease symptoms or prevent or treat the disease relate to compounds characterized by the following structure: STR1 and their pharmaceutically acceptable salts. Y is selected from the group consisting of oxygen, sulfur, sulfonyl, sulfinyl, and --NR7 --. R1 is --TR8, where T is --C(X1)-- or --SO2 --, and R8 is selected from the group consisting of --OR9, --NHNHSO2 R9, --NHNHC(X2)OR9, --NR9 R10, --NHNHC(X2)NR9 R10, --NHCR9 R10 C(X2)NR11 R12, --NHC(X2)NR9 R10, and the piperazinyl moiety shown below: STR2 where n is 0 or 1, and Qn, for n=1, is --SO2 --, --C(X2)-- or --C(X2)NR10 --. R2 -R6 are selected independently from the group consisting of hydrogen, alkyl, aryl, hydroxyl, alkoxyl, aryloxyl, aralkoxyl, halogen, cyano, nitro, alkylcarbamido, arylcarbamido, dialkylcarbamido, diarylcarbamido, alkylarylcarbamido, alkylthiocarbamido, arylthiocarbamido, dialkylthiocarbamido, diarylthiocarbamido, alkylarylthiocarbamido, amino, alkylamino, arylamino, dialkylamino, diarylamino, arylalkylamino, aminocarbonyl, alkylaminocarbonyl, arylaminocarbonyl, dialkylaminocarbonyl, diarylaminocarbonyl, arylalkylaminocarbonyl, alkylcarbonyloxy, arylcarbonyloxy, carboxyl, alkoxycarbonyl, aryloxycarbonyl, sulfo, alkylsulfonylamido, arylsulfonylamido, alkylsulfonyl, arylsulfonyl, alkylsulfinyl, and arylsulfinyl. X1 and X2 are selected independently from the group consisting of oxygen, and sulfur. R7 -R12 are selected independently from the group consisting of hydrogen, alkyl, aryl, aralkyl, heterocycle, and heterocyclealkyl.

Process for the synthesis of 3-chlorobenzo[b]thiophene-2-carbonyl chlorides

An improved process for the preparation of 3-chlorobenzo[b]thiophene-2-carbonyl chlorides is described where a cinnamic acid is converted in the presence of thionyl chloride and a 4-N,N'-disubstituted aminopyridine in one step to the desired product.