1034305-11-7

Basic information

• Product Name: Benzo[b]thiophene-2-Methanol, α-(5-broMo-2-fluorophenyl)-
• Synonyms: Benzo[b]thiophene-2-Methanol, α-(5-broMo-2-fluorophenyl)-;benzo[b]thiophen-2-yl(5-broMo-2-fluorophenyl)Methanol;Ipragliflozin interMdiate;1-benzothien-2-yl(5-bromo-2-fluorophenyl)methanol
• CAS NO: 1034305-11-7
• Molecular Formula: C₁₅H₁₀BrFOS
• Molecular Weight: 337.2067032
• Mol File: 1034305-11-7.mol

Chemical Properties

• Boiling Point: 458.7±40.0 °C(Predicted)
• Appearance: /
• Density: 1.597±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 12.52±0.20(Predicted)
• CAS DataBase Reference: Benzo[b]thiophene-2-Methanol, α-(5-broMo-2-fluorophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzo[b]thiophene-2-Methanol, α-(5-broMo-2-fluorophenyl)-(1034305-11-7)
• EPA Substance Registry System: Benzo[b]thiophene-2-Methanol, α-(5-broMo-2-fluorophenyl)-(1034305-11-7)

Safety Data

• Hazardous Substances Data: 1034305-11-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
Benzo[b]thiophene-2-Methanol, α-(5-bromo-2-fluorophenyl)is used as a crucial intermediate in the synthesis of various pharmaceutical drugs. Its unique structure and functional groups make it a valuable component in the development of new medications with specific therapeutic properties.
Used in Biochemical Research:
In the field of biochemical research, Benzo[b]thiophene-2-Methanol, α-(5-bromo-2-fluorophenyl)serves as an essential tool for studying biological processes and mechanisms. Its presence in experimental compounds allows researchers to investigate the interactions between this chemical and biological systems, contributing to a deeper understanding of molecular biology and potential therapeutic applications.
Used in Drug Synthesis:
Benzo[b]thiophene-2-Methanol, α-(5-bromo-2-fluorophenyl)is used as a key component in the synthesis of various drugs, particularly those targeting specific diseases or conditions. Its unique structure and functional groups enable the development of drugs with improved efficacy, selectivity, and reduced side effects.
Used in Medicinal Chemistry:
In medicinal chemistry, Benzo[b]thiophene-2-Methanol, α-(5-bromo-2-fluorophenyl)is employed as a building block for the design and synthesis of novel compounds with potential therapeutic applications. Its versatility and reactivity make it an attractive candidate for the development of new drugs and drug candidates.
Used in Drug Discovery:
Benzo[b]thiophene-2-Methanol, α-(5-bromo-2-fluorophenyl)is utilized in drug discovery processes to identify and optimize potential drug candidates. Its unique properties and reactivity allow researchers to explore new chemical space and discover novel compounds with promising therapeutic potential.
Used in Chemical Synthesis:
In the broader field of chemical synthesis, Benzo[b]thiophene-2-Methanol, α-(5-bromo-2-fluorophenyl)is employed as a versatile intermediate for the preparation of various organic compounds. Its unique structure and functional groups enable the synthesis of a wide range of chemical products, including specialty chemicals, agrochemicals, and materials.

Upstream product

• 93777-26-5 5-bromo-2-fluorobenzaldehyde 
• 95-15-8 Benzo[b]thiophene 
• 94569-84-3 2-bromo-5-fluorobenzaldehyde 

Downstream Products

• 1034305-19-5 2-[(5-bromo-2-fluorophenyl)(chloro)methyl]-1-benzothiophene 
• 951382-34-6 Ipragliflozin L-proline 
• 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 
• 761423-01-2 (1S)-1,5-anhydro-1-[3-(1-benzothiophen-2-ylmethyl)-4-fluorophenyl]-2,3,4,6-tetra-O-benzyl - D-glucitol 
• 1034305-17-3 2-[(5-bromo-2-fluorophenyl)methyl]-1-benzothiophene 
• 761424-75-3 [1-benzothiene-2-yl-(5-bromo-2-fluorophenyl)methoxy](tert-butyl)dimethylsilane 

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.