154630-32-7

Basic information

• Product Name: 5-FLUORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER
• Synonyms: METHYL 5-FLUORO-1-BENZOTHIOPHENE-2-CARBOXYLATE;5-FLUORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER;5-Fluoro-2-(methoxycarbonyl)benzo[b]thiophene;Ethyl 5-fluorobenzo[b]thiophene-2-carboxylate, 96%
• CAS NO: 154630-32-7
• Molecular Formula: C₁₀H₇FO₂S
• Molecular Weight: 210.22
• Mol File: 154630-32-7.mol

Chemical Properties

• Melting Point: 80-82°C
• Boiling Point: 308.344 °C at 760 mmHg
• Flash Point: 140.281 °C
• Appearance: /
• Density: 1.355 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.617
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5-FLUORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 5-FLUORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER(154630-32-7)
• EPA Substance Registry System: 5-FLUORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER(154630-32-7)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 154630-32-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
5-FLUORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its role in the development of new drugs is significant due to its potential medicinal properties, which make it a subject of interest for scientists and researchers in pharmacology.
Used in Organic Synthesis:
In the field of organic chemistry, 5-FLUORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER is employed as a building block for the creation of complex organic molecules. Its unique structure allows for versatile reactions and transformations, contributing to the advancement of organic synthesis techniques.
Used in Medicinal Chemistry:
5-FLUORO-BENZO[B]THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER is utilized as a starting material in the design and synthesis of novel therapeutic agents. Its potential to be incorporated into drug molecules makes it a valuable resource for medicinal chemists working on the next generation of medications.

InChI:InChI=1/C10H7FO2S/c1-13-10(12)9-5-6-4-7(11)2-3-8(6)14-9/h2-5H,1H3

Upstream product

• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 1191415-34-5 2-(2,2-dibromovinyl)-4-fluorobenzenethiol 
• 70060-12-7 5-fluorobenzo[b]thiophene 
• 124-38-9 carbon dioxide 
• 74-88-4 methyl iodide 
• 2646-90-4 2,5-difluorobenzaldehyde 
• 2365-48-2 Methyl thioglycolate 

Downstream Products

• 13771-73-8 (5-fluorobenzo[b]thiophen-2-yl)methanol 
• 70060-12-7 5-fluorobenzo[b]thiophene 
• 70060-13-8 5-fluorobenzo[b]thiophene-2-carboxylic acid 
• 698367-29-2 5-fluorobenzo[b]thiophene-2-carboxaldehyde 

Relevant articles and documents

Design, synthesis, and biological activity evaluation of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives as broad-spectrum antifungal agents

To discover antifungal compounds with broad-spectrum and stable metabolism, a series of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives was designed and synthesized. Compounds A30-A34 exhibited excellent broad-spectrum antifungal activity against Candida albicans with MIC values in the range of 0.03–0.5 μg/mL, and against Cryptococcus neoformans and Aspergillus fumigatus with MIC values in the range of 0.25–2 μg/mL. In addition, compounds A31 and A33 showed high metabolic stability in human liver microsomes in vitro, with the half-life of 80.5 min and 69.4 min, respectively. Moreover, compounds A31 and A33 showed weak or almost no inhibitory effect on the CYP3A4 and CYP2D6. The pharmacokinetic evaluation in SD rats showed that compound A31 had suitable pharmacokinetic properties and was worthy of further study.

Direct Carboxylation of Electron-Rich Heteroarenes Promoted by LiO-tBu with CsF and [18]Crown-6

We herein demonstrate that the combination of LiO-tBu, CsF, and [18]crown-6 efficiently promotes the direct C?H carboxylation of electron-rich heteroarenes (benzothiophene, thiophene, benzofuran, and furan derivatives). A variety of functional groups, including methyl, methoxy, halo, cyano, amide, and keto moieties, are compatible with this system. The reaction proceeds via the formation of a tert-butyl carbonate species.

Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?

The syntheses and antiplasmodial activities of various substituted aminoquinolines coupled to an adamantane carrier are described. The compounds exhibited pronounced in vitro and in vivo activity against Plasmodium berghei in the Thompson test. Tethering a fluorine atom to the aminoquinoline C(3) position afforded fluoroaminoquinolines that act as intrahepatocytic parasite inhibitors, with compound 25 having an IC50 = 0.31 μM and reducing the liver load in mice by up to 92% at 80 mg/kg dose. Screening our peroxides as inhibitors of liver stage infection revealed that the tetraoxane pharmacophore itself is also an excellent liver stage P. berghei inhibitor (78: IC50 = 0.33 μM). Up to 91% reduction of the parasite liver load in mice was achieved at 100 mg/kg. Examination of tetraoxane 78 against the transgenic 3D7 strain expressing luciferase under a gametocyte-specific promoter revealed its activity against stage IV-V Plasmodium falciparum gametocytes (IC50 = 1.16 ± 0.37 μM). To the best of our knowledge, compounds 25 and 78 are the first examples of either an 4-aminoquinoline or a tetraoxane liver stage inhibitors.

Benzo[b]thiophene-2-carboxamide derivatives as potent urotensin-II receptor antagonists

Members of a series of benzo[b]thiophene-2-carboxamide derivatives, possessing an N-(1-(3-bromo-4-(piperidin-4-yloxy)benzyl)piperidin-4-yl) group, were synthesized and evaluated as urotensin-II receptor antagonists. The results show that these substances have potent UT binding affinities. Observations made in a systematic SAR investigation of the effects of a variety of substituents (R1and R2) at the 5- and 6-positions in the benzo[b]thiophene-2-carboxamide moiety on UT binding affinities led to identification of the 5-cyano analog 7f as a highly potent UT antagonist with an IC50value of 25?nM. Despite having a good metabolic stability, 7f is a potent inhibitor of CYP isozyme and displays an unsuitable PK profile.

17a-HYDROXYLASE/C17,20-LYASE INHIBITORS

The present invention provides compounds of Formula (I), or a pharmaceutically acceptable salt thereof, where R1, R2, R3, R4, R5, R6, A and n are as defined herein. A deuteriated derivative of the compound of Formula (I) is also provided.

17α-HYDROXYLASE/C17,20-LYASE INHIBITORS

The present invention provides compounds of Formula (I), or a pharmaceutically acceptable salt thereof, where R1, R2, R3, R4, R5, R6, A and n are as defined herein. A deuteriated derivative of the compound of Formula (I) is also provided.

Palladium-catalyzed domino C-S coupling/carbonylation reactions: An efficient synthesis of 2-carbonylbenzo[ b ]thiophene derivatives

A facile and selective palladium-catalyzed domino procedure has been developed for the preparation of 2-carbonylbenzo[b]thiophene derivatives from 2-gem-dihalovinylthiophenols. This protocol involves intramolecular C-S coupling/intermolecular carbonylatio