1034305-17-3

Basic information

• Product Name: Benzo[b]thiophene, 2-[(5-broMo-2-fluorophenyl)Methyl]-
• Synonyms: Benzo[b]thiophene, 2-[(5-broMo-2-fluorophenyl)Methyl]-;2-(5-BroMo-2-fluorobenzyl)benzothiophene;2-(5-BroMo-2-fluorobenzyl)benzo[b]thiophene;2-[(5-bromo-2-fluorophenyl)Methyl]-Benzo[b]thiophene;2-(5-bromo-2-fluorobenzyl)-1-benzothiophene;2-[(5-bromo-2-fluorophenyl)methyl]-1-benzothiophene;Ipragliflozin impurity B (B4);2-[(5-broMo-2-fluorophenyl)Methyl]-
• CAS NO: 1034305-17-3
• Molecular Formula: C₁₅H₁₀BrFS
• Molecular Weight: 321.2073032
• Mol File: 1034305-17-3.mol

Chemical Properties

• Boiling Point: 408.9±35.0 °C(Predicted)
• Appearance: /
• Density: 1.509±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: Benzo[b]thiophene, 2-[(5-broMo-2-fluorophenyl)Methyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzo[b]thiophene, 2-[(5-broMo-2-fluorophenyl)Methyl]-(1034305-17-3)
• EPA Substance Registry System: Benzo[b]thiophene, 2-[(5-broMo-2-fluorophenyl)Methyl]-(1034305-17-3)

Safety Data

• Hazardous Substances Data: 1034305-17-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Benzo[b]thiophene, 2-[(5-bromo-2-fluorophenyl)methyl]is utilized as a building block in the synthesis of new drugs due to its unique molecular structure and potential biological activities. It is particularly valuable for its role in the development of pharmaceuticals with anti-cancer, anti-inflammatory, and antibacterial properties.
Used in Agrochemical Industry:
In the agrochemical sector, Benzo[b]thiophene, 2-[(5-bromo-2-fluorophenyl)methyl]serves as a key component in the creation of new agrochemicals, leveraging its chemical properties to enhance the effectiveness of products designed for agricultural applications.
Used in Materials Science:
Benzo[b]thiophene, 2-[(5-bromo-2-fluorophenyl)methyl]is also employed in materials science for the development of novel materials, capitalizing on its structural attributes to improve material properties or introduce new functionalities.
Used in Medicinal Chemistry Research:
Benzo[b]thiophene, 2-[(5-broMo-2-fluorophenyl)Methyl]is applied in medicinal chemistry research as a promising candidate for exploring its biological activities and potential therapeutic effects, with a focus on its anti-cancer, anti-inflammatory, and antibacterial properties, which could lead to the discovery of new treatments and therapies.

Upstream product

• 1034305-19-5 2-[(5-bromo-2-fluorophenyl)(chloro)methyl]-1-benzothiophene 
• 95-15-8 Benzo[b]thiophene 
• 93777-26-5 5-bromo-2-fluorobenzaldehyde 
• 1034305-11-7 (1-benzothiophen-2-yl)(5-bromo-2-fluorophenyl)methanol 

Downstream Products

• 1034305-23-1 methyl 1-C-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-α-glucopyranoside 
• 761423-01-2 (1S)-1,5-anhydro-1-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-2,3,4,6-tetra-O-benzyl - D-glucitol 
• 761423-87-4 (2S,3R,4R,5S,6R)-2-(3-(benzo[b]thiophen-2-ylmethyl)-4-fluorophenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 1034305-21-9 (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-[3-[(1-benzothiophen-2-yl)methyl]-4-fluorophenyl]-D-sorbitol 
• 951382-34-6 Ipragliflozin L-proline 
• 1034305-27-5 methyl 2,3,4,6-tetra-O-acetyl-1-C-[3-(1-benzothien-2-ylmethyl)-4-fluorophenyl]-α-glucopyranoside 

Relevant articles and documents

Method for synthesizing ipragliflozin

The invention discloses a method for synthesizing ipragliflozin. The method comprises the following steps: (1) generating alkylation reaction by formula-4 compound and formula-5 compound to generate aformula-6 compound; (2) carrying out deprotection on the formula-6 compound to generate a formula-7 compound, i.e., ipragliflozin. Compared with the prior art, the preparation method disclosed by theinvention is characterized in that adopted starting raw materials are cheap and can be easily obtained, a synthesis route is short, operation is convenient, cost is lower and general yield is high. The method conforms to the concept of green chemistry and is suitable for industrial production. (The formulas are shown in the description.).

Synthesis method for 2-(5-bromo-2-fluorobenzyl)benzothiophene

The invention discloses a synthesis method for 2-(5-bromo-2-fluorobenzyl)benzothiophene. The synthetic method is characterized in that 2-fluoro-5-bromobenzaldehyde is taken as a raw material, and a target compound is obtained through condensation and reduction under action of alkaline; and the synthetic method comprises condensation reaction and reduction reaction. The synthesis method can be usedfor obtaining the target product through two-step reaction, so that material varieties are reduced, and operation efficiency is improved. Chemicals such as boron trifluoride diethyl ether are not used, and reducing agents which are not suitable for industrial amplification such as sodium borohydride are not used, so that the production cost is reduced while an ultra-low temperature is not needed.The synthesis method has characteristics of being mild in reaction conditions, simple in process operation, green and environmentally friendly, low in cost, and high in yield.

Discovery of Ipragliflozin (ASP1941): A novel C-glucoside with benzothiophene structure as a potent and selective sodium glucose co-transporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes mellitus

A series of C-glucosides with various heteroaromatics has been synthesized and its inhibitory activity toward SGLTs was evaluated. Upon screening several compounds, the benzothiophene derivative (14a) was found to have potent inhibitory activity against SGLT2 and good selectivity versus SGLT1. Through further optimization of 14a, a novel benzothiophene derivative (14h; ipragliflozin, ASP1941) was discovered as a highly potent and selective SGLT2 inhibitor that reduced blood glucose levels in a dose-dependent manner in diabetic models KK-Ay mice and STZ rats.

METHOD FOR PRODUCING C-GLYCOSIDE DERIVATIVE AND SYNTHETIC INTERMEDIATE THEREOF

The present invention provides a method for producing a C-glycoside derivative, which can produce the C-glycoside derivative at a high yield and at a low cost, which conforms to environmental protection, and which is applicable industrially. The C-glycoside derivative is useful for treating and preventing diabetes such as insulin-dependent diabetes (type 1 diabetes), non-insulin-dependent diabetes (type 2 diabetes) and the like and various diabetes-related diseases including insulin-resistant diseases and obesity.