4463-59-6

Basic information

• Product Name: 2-(2-Bromoethoxy)anisole
• Synonyms: 1-(2-Bromethoxy)-2-methoxy-benzol;2-(2-BROMOETHOXY)ANISOLE 98%;2-(2-Bromoethoxy)ani;2-(2-BroMoethoxy)anisole, 97+%;AKOS BC-2659;2-(2-BROMOETHOXY)ANISOLE;2-(2-BROMOETHOXY)-METHOXYBENZENE;2-(2-BROMOETHOXY)-1-METHOXYBENZENE
• CAS NO: 4463-59-6
• Molecular Formula: C₉H₁₁BrO₂
• Molecular Weight: 231.09
• EINECS: 402-010-4
• Product Categories: Anisole
• Mol File: 4463-59-6.mol
• Article Data: 19

Chemical Properties

• Melting Point: 43-45 °C(Solv: ethanol (64-17-5))
• Boiling Point: 270.3 °C at 760 mmHg
• Flash Point: 114 °C
• Appearance: /
• Density: 1.382 g/cm³
• Vapor Pressure: 0.0115mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-(2-Bromoethoxy)anisole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-Bromoethoxy)anisole(4463-59-6)
• EPA Substance Registry System: 2-(2-Bromoethoxy)anisole(4463-59-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-52/53
• Safety Statements: 22-61
• HazardClass: IRRITANT
• Hazardous Substances Data: 4463-59-6(Hazardous Substances Data)

Usage

General Description

2-(2-Bromoethoxy)anisole is a chemical compound that is commonly used as a building block in organic synthesis. It is a white solid that has a slight aromatic odor, and it is insoluble in water but soluble in organic solvents such as ethanol and ether. It is primarily used as an intermediate in the production of pharmaceuticals, agrochemicals, and other specialty chemicals. Its chemical structure consists of an anisole group, which is a benzene ring with a methoxy group attached, and a bromoethoxy group, which is a bromine atom bonded to an ethoxy group. 2-(2-Bromoethoxy)anisole is known to be a skin and eye irritant and should be handled with care.

InChI:InChI=1/C9H11BrO2/c1-11-8-4-2-3-5-9(8)12-7-6-10/h2-5H,6-7H2,1H3

Upstream product

• 90-05-1 2-methoxy-phenol 
• 106-93-4 ethylene dibromide 
• 540-51-2 2-bromoethanol 

Downstream Products

• 15687-23-7 diethyl-[2-(2-methoxy-phenoxy)-ethyl]-amine 
• 10461-19-5 bis-(2-hydroxy-ethyl)-[2-(2-methoxy-phenoxy)-ethyl]-amine 
• 1836-62-0 2-(2-methoxy-phenoxy)-ethylamine 
• 3258-70-6 2-(2-methoxyphenoxy)-N-[2-(2-methoxyphenoxy)ethyl]ethanamine 
• 7784-99-8 1-methoxy-2-vinyloxybenzene 
• 47451-66-1 6-[2-(2-methoxy-phenoxy)-ethyl]-5-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline 
• 3244-08-4 N-<2-<-(2-Methoxy-phenoxy)-aethylamino>-aethyl>-2-methoxy-anilin 
• 3244-05-1 N-<2-(2-Methoxy-phenoxy)-aethyl>-N-<3-(2-methoxy-phenoxy)-propyl>-hydrazin 
• 3244-07-3 N,N'-Bis-<2-(2-Methoxy-phenoxy)-aethyl>-propan 
• 3246-04-6 N-<2-(2-Methoxy-phenoxy)-aethyl>-butylamin 
• 163764-52-1 N-[β-(2-methoxyphenoxy)ethyl]-α,γ-diaminopropane 
• 3317-51-9 N-<2-(2-Methoxy-phenoxy)-aethyl>-3-hydroxy-propylamin 
• 3246-03-5 N-[2-(2'-(methoxy)-phenoxy)-ethyl]-benzylamine 
• 3246-01-3 2-(2-Methoxy-phenoxy)-aethylhydrazin 

Relevant articles and documents

Design and synthesis of new potent 5-HT7 receptor ligands as a candidate for the treatment of central nervous system diseases

Owing to their multifunctional pharmacological profiles (including dual 5-HT1A/5-HT7 action), arylpiperazine derivatives are widely used for treating central nervous system diseases including the depression or neuropathic pain. Herein we describe the design, synthesis and evaluation of biological activity of novel 5-HT7 ligands derived of 2,4,6-triamino-1,3,5-triazine. The studied compounds showed affinity and high selectively towards 5-HT7 receptor with the two most active compounds 34 (Ki = 61 nM), 22 (Ki = 109 nM) showing good metabolic stability and moderate affinity to CYP3A4 isoenzyme. Compound 22 had high hepatotoxicity at a concentration below 50 μM, while compound 34 showed low hepatotoxicity even at a concentration above 50 μM.

Discovery, Optimization, and Characterization of ML417: A Novel and Highly Selective D3 Dopamine Receptor Agonist

To identify novel D3 dopamine receptor (D3R) agonists, we conducted a high-throughput screen using a β-arrestin recruitment assay. Counterscreening of the hit compounds provided an assessment of their selectivity, efficacy, and potency. The most promising scaffold was optimized through medicinal chemistry resulting in enhanced potency and selectivity. The optimized compound, ML417 (20), potently promotes D3R-mediated β-arrestin translocation, G protein activation, and ERK1/2 phosphorylation (pERK) while lacking activity at other dopamine receptors. Screening of ML417 against multiple G protein-coupled receptors revealed exceptional global selectivity. Molecular modeling suggests that ML417 interacts with the D3R in a unique manner, possibly explaining its remarkable selectivity. ML417 was also found to protect against neurodegeneration of dopaminergic neurons derived from iPSCs. Together with promising pharmacokinetics and toxicology profiles, these results suggest that ML417 is a novel and uniquely selective D3R agonist that may serve as both a research tool and a therapeutic lead for the treatment of neuropsychiatric disorders.

Synthesis and Investigation of S-Substituted 2-Mercaptobenzoimidazoles as Inhibitors of Hedgehog Signaling

Due to the arising resistance of common drugs targeting the Hedgehog signaling pathway, the identification of new compound classes with inhibitory effect is urgently needed. We were able to identify S-alkylated 2-mercaptobenzoimidazoles as a new compound