34576-87-9

Basic information

• Product Name: 3-CHLORO-6-METHYL-BENZO[B]THIOPHENE-2-CARBONYL CHLORIDE
• Synonyms: 3-CHLORO-6-METHYL-BENZO[B]THIOPHENE-2-CARBONYL CHLORIDE;AKOS B000008
• CAS NO: 34576-87-9
• Molecular Formula: C₁₀H₆Cl₂OS
• Molecular Weight: 245.13
• Mol File: 34576-87-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 357.606 °C at 760 mmHg
• Flash Point: 170.074 °C
• Appearance: /
• Density: 1.462 g/cm³
• Storage Temp.: 2-8°C
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 3-CHLORO-6-METHYL-BENZO[B]THIOPHENE-2-CARBONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CHLORO-6-METHYL-BENZO[B]THIOPHENE-2-CARBONYL CHLORIDE(34576-87-9)
• EPA Substance Registry System: 3-CHLORO-6-METHYL-BENZO[B]THIOPHENE-2-CARBONYL CHLORIDE(34576-87-9)

Safety Data

• Hazard Codes: 8:
• RIDADR: UN3261
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 34576-87-9(Hazardous Substances Data)

Usage

General Description

3-CHLORO-6-METHYL-BENZO[B]THIOPHENE-2-CARBONYL CHLORIDE is a chemical compound that belongs to the class of benzo[b]thiophene derivatives. It is a carbonyl chloride derivative, which means it contains a carbonyl group and a chlorine atom. 3-CHLORO-6-METHYL-BENZO[B]THIOPHENE-2-CARBONYL CHLORIDE is often used in the pharmaceutical industry as an intermediate in the synthesis of various drugs and biologically active molecules. It can also be used in research and development for the creation of new compounds with potential therapeutic applications. Additionally, it is a valuable reagent in organic synthesis, particularly in the formation of carbon-carbon and carbon-heteroatom bonds. Due to its chemical properties and versatile applications, 3-CHLORO-6-METHYL-BENZO[B]THIOPHENE-2-CARBONYL CHLORIDE is an important compound in the field of organic chemistry and drug discovery.

Upstream product

• 14290-88-1 (2Z)-3-(4-methylphenyl)propenoic acid 
• 1866-39-3 trans-p-methylcinnamic acid 
• 7141-87-9 α-Brom-p-methyl-hydrozimtsaeure 
• 1866-39-3 4-methylcinnamic acid 

Downstream Products

• 229339-69-9 N-(4-chlorophenyl)-2-[((3-chloro-6-methylbenzo[b]thien-2-yl)carbonyl)amino]-5-chlorobenzamide 
• 59812-34-9 methyl 3-chloro-6-methylbenzothiophene-2-carboxylate 
• 1381771-25-0 N-(4-carboxyphenyl)-6-methyl-3-chlorobenzo[b]thiophene-2-carboxamide 
• 1381771-35-2 6-methyl-2-{N-[4-N-(3-dimethylamino)propyl]carbamoyl}-3-chlorobenzo[b]thiophene anilide 
• 1381771-30-7 N-(4-chlorocarbonylphenyl)-6-methyl-3-chlorobenzo[b]thiophene-2-carboxamide 
• 84258-87-7 3-chloro-6-methyl-2-styrylbenzothiophene 
• 84258-86-6 3-chloro-6-methylbenzothiophene-2-carboxaldehyde 
• 72870-78-1 3-Chlor-N-<(dimethylamino)(4-methoxyphenylamino)methylen>-6-methylbenzothiophen-2-carboxamid 
• 72858-21-0 3-Chlor-N-<(dimethylamino)(p-tolylthio)methylen>-6-methylbenzothiophen-2-carboxamid 
• 34586-87-3 3-Chlor-6-methylbenzothiophen-2-carboxamid 
• 725712-44-7 1-(3-chloro-6-methyl-benzo[b]thiophene-2-carbonyl)-3-p-tolyl-thiourea 
• 725712-43-6 1-(3-chloro-6-methyl-benzo[b]thiophene-2-carbonyl)-3-phenyl-thiourea 
• 95458-28-9 3-Chloro-6-methyl-benzo[b]thiophene-2-carboxylic acid (3-imidazol-1-yl-propyl)-amide 

Relevant articles and documents

Accepting the Invitation to Open Innovation in Malaria Drug Discovery: Synthesis, Biological Evaluation, and Investigation on the Structure-Activity Relationships of Benzo[b]thiophene-2-carboxamides as Antimalarial Agents

Malaria eradication is a global health priority, but current therapies are not always suitable for providing a radical cure. Artemisinin has paved the way for the current malaria treatment, the so-called Artemisinin-based Combination Therapy (ACT). However, with the detection of resistance to ACT, innovative compounds active against multiple parasite species and at multiple life stages are needed. GlaxoSmithKline has recently disclosed the results of a phenotypic screening of an internal library, publishing a collection of 400 antimalarial chemotypes, termed the “Malaria Box”. After analysis of the data set, we have carried out a medicinal chemistry campaign in order to define the structure-activity relationships for one of the released compounds, which embodies a benzothiophene-2-carboxamide core. Thirty-five compounds were prepared, and a description of the structural features responsible for the in vitro activity against different strains of P. falciparum, the toxicity, and the metabolic stability is herein reported.

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.

SYNTHESIS AND SOME TRANSFORMATIONS OF BENZOTHIOPHENE DERIVATIVES

A number of 3-chloro-2-chlorocarbonylbenzothiophenes with alkyl substituents in various positions of the benzene ring were synthesized by arylation of acrylic acid with the corresponding alkyl-substituted iodobenzenes under the influence of catalytic amounts of palladium acetate and subsequent oxidation of the resulting arylacrylic acids with thionyl chloride.Replacement of the pyridine added in the oxidation reaction by triethylbenzylammonium chloride led to substantial increases in the yields of the desired products.The possibility of conversionof the resulting benzothiophene derivatives to thiophene ring-unsubstituted benzothiophenes was shown in the case of 3-chloro-2-chlorocarbonylbenzothiophene as a result of successive saponification of the 2-chlorocarbonyl group, decarboxylation, and dechlorination.