196597-67-8

Basic information

• Product Name: Ethyl 3-(7-Bromo-2,3-dihydro-1-benzofuran-5-yl)propanoate
• Synonyms: 3-(7-Bromo-2,3-dihydrobenzo[b]furan-5-yl)propanoic Acid Ethyl Ester;7-Bromo-2,3-dihydro-5-benzofuranpropanoic Acid Ethyl Ester;Ethyl 3-(7-Bromo-2,3-dihydro-1-benzofuran-5-yl)propanoate;5-Benzofuranpropanoic acid, 7-bromo-2,3-dihydro-, ethyl ester;Ethyl 3-(7-bromo-2,3-dihydrobenzofuran-5-yl)propanoate
• CAS NO: 196597-67-8
• Molecular Formula: C₁₃H₁₅BrO₃
• Molecular Weight: 299.16
• Product Categories: Aromatics Compounds;Aromatics;Heterocycles;Aromatics, Heterocycles
• Mol File: 196597-67-8.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 374.5°C at 760 mmHg
• Flash Point: 180.3°C
• Appearance: /
• Density: 1.413g/cm³
• Vapor Pressure: 8.3E-06mmHg at 25°C
• Refractive Index: 1.559
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: Ethyl 3-(7-Bromo-2,3-dihydro-1-benzofuran-5-yl)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 3-(7-Bromo-2,3-dihydro-1-benzofuran-5-yl)propanoate(196597-67-8)
• EPA Substance Registry System: Ethyl 3-(7-Bromo-2,3-dihydro-1-benzofuran-5-yl)propanoate(196597-67-8)

Safety Data

• Hazardous Substances Data: 196597-67-8(Hazardous Substances Data)

Usage

Description

Ethyl 3-(7-Bromo-2,3-dihydro-1-benzofuran-5-yl)propanoate is a chemical compound characterized by its white solid appearance. It is a derivative of benzofuran, a type of organic compound that contains a fused benzene and furan ring. The presence of a bromine atom and an ethyl ester group in its structure contributes to its unique chemical properties and potential applications.

Uses

1. Used in Pharmaceutical Industry:
Ethyl 3-(7-Bromo-2,3-dihydro-1-benzofuran-5-yl)propanoate is used as a receptor agonist for the treatment of sleep disorders. Its chemical structure allows it to interact with specific receptors in the body, potentially modulating the sleep-wake cycle and providing therapeutic benefits for individuals suffering from sleep-related conditions.
2. Used in Chemical Research:
As a chemical compound with unique structural features, Ethyl 3-(7-Bromo-2,3-dihydro-1-benzofuran-5-yl)propanoate can be utilized in various research applications. It may serve as a starting material or intermediate in the synthesis of other complex organic molecules, particularly those with potential pharmaceutical or biological significance.
3. Used in Material Science:
The compound's chemical properties, including its white solid appearance and structural features, may also make it suitable for use in the development of new materials with specific properties. For example, it could be explored for its potential applications in the creation of novel polymers, coatings, or other advanced materials with tailored characteristics.

InChI:InChI=1/C13H15BrO3/c1-2-16-12(15)4-3-9-7-10-5-6-17-13(10)11(14)8-9/h7-8H,2-6H2,1H3

Upstream product

• 196597-65-6 ethyl (E)-3-(2,3-dihydrobenzofuran-5-yl)-2-propenoate 
• 55745-70-5 2,3-dihydro-benzofuran-5-carbaldehyde 
• 496-16-2 2.3-dihydrobenzofuran 
• 196597-66-7 ethyl 3-(2,3-dihydro-1-benzofuran-5-yl)propanoate 

Downstream Products

• 196597-68-9 3-(7-bromo-2,3-dihydrobenzofuran-5-yl)propionic acid 
• 196597-27-0 N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]propionamide 
• 196597-16-7 N-[2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethyl]acetylamide 
• 196597-76-9 ethyl 3-(6,7-dibromo-2,3-dihydrobenzofuran-5-yl) propionic acid 
• 196597-77-0 4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one 
• 196597-79-2 (E)-2-(1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-ylidene)acetonitrile 
• 448964-37-2 2?(1,6,7,8?tetrahydro?2H?indeno[5,4?b]furan?8?yl)?1?ethylamine 
• 196597-78-1 1,2,6,7-tetrahydro-8H-indeno[5,4-b]-furan-8-one 
• 196597-75-8 ethyl 3-(6,7-dibromo-2,3-dihydro-1-benzofuran-5-yl)propanoate 

Relevant articles and documents

Synthesis of a novel series of tricyclic indan derivatives as melatonin receptor agonists

To develop a new therapeutic agent for sleep disorders, we synthesized a novel series of tricyclic indan derivatives and evaluated them for their binding affinity to melatonin receptors. In our previous paper, we proposed a conformation of the methoxy group favorable for the binding of the MT1 receptor. To fix the methoxy group in an active conformation, we decided to synthesize conformationally restricted tricyclic indan analogues with the oxygen atom in the 6-position incorporated into a furan, 1,3-dioxane, oxazole, pyran, morpholine, or 1,4-dioxane ring system. Among these compounds, indeno[5,4-b]furan analogues were found to be the most potent and selective MT1 receptor ligands and to have superior metabolic stability. The optimization of substituents led to (S)-(-)-22b, which showed very strong affinity for human MT1 (Ki = 0.014 nM), but no significant affinity for hamster MT3 (Ki = 2600 nM) or other neurotransmitter receptors. The pharmacological effects of (S)-(-)-22b were studied in experimental animals, and it was found that a dose of 0.1 mg/kg, po promoted a sleep in freely moving cats, as demonstrated by a decrease in wakefulness and increases in slow wave sleep and rapid eye movement sleep, which lasted for 6 h after administration. Melatonin (1 mg/kg, po) also had a sleep-promoting effect, though it lasted only 2 h. A new chiral method for the synthesis of (S)-(-)-22b starting from 60, which was prepared from 59 employing asymmetric hydrogenation with the (S)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl-Ru complex, was developed. (S)-(-)-22b (TAK-375) is currently under clinical trial for the treatment of insomnia and circadian rhythm disorders.