50366-31-9

Basic information

• Product Name: Benzene, 1,1'-[(2-chloroethoxy)methylene]bis[4-fluoro-
• CAS NO: 50366-31-9
• Molecular Formula: C15H13ClF2O
• Molecular Weight: 282.717
• Mol File: 50366-31-9.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: Benzene, 1,1'-[(2-chloroethoxy)methylene]bis[4-fluoro-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,1'-[(2-chloroethoxy)methylene]bis[4-fluoro-(50366-31-9)
• EPA Substance Registry System: Benzene, 1,1'-[(2-chloroethoxy)methylene]bis[4-fluoro-(50366-31-9)

Safety Data

• Hazardous Substances Data: 50366-31-9(Hazardous Substances Data)

Upstream product

• 365-24-2 4,4'-difluorobenzhydryl alcohol 
• 107-07-3 2-chloro-ethanol 
• 104-15-4 toluene-4-sulfonic acid 
• 352-13-6 4-flourophenylmagnesium bromide 

Downstream Products

• 138522-66-4 1-<2-bis(4-fluorophenyl)methoxyethyl>-4-cyanopiperidine 
• 131278-85-8 ethyl 1-<2-bis(4-fluorophenyl)methoxyethyl>-4-piperidinecarboxylate 
• 67469-45-8 GBR 13069 dihydrochloride 
• 150557-06-5 1-{2-[bis(4-fluorophenyl)methoxy]ethyl}homopiperazine 
• 777833-33-7 (S)-1-{2-[Bis-(4-fluoro-phenyl)-methoxy]-ethyl}-pyrrolidine-2-carboxylic acid amide 
• 163181-22-4 (2R,5S)-1-{2-[Bis-(4-fluoro-phenyl)-methoxy]-ethyl}-2,5-dimethyl-piperazine 
• 163181-23-5 (2S,5R)-1-{2-[Bis-(4-fluoro-phenyl)-methoxy]-ethyl}-2,5-dimethyl-piperazine 
• 131278-94-9 1-<2-bis(4-fluorophenyl)methoxyethyl>-4-piperidinol 
• 96122-69-9 1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]pyrrolidine 
• 104586-94-9 9-[2-[Bis(4-fluorophenyl)methoxy]ethylamino]-3,4-dihydroacridin-1(2H)-one, maleate 
• 88166-50-1 1'-[2-[bis(4-fluorophenyl)methoxy]ethyl]-2-methylspiro[2H-1,4-benzodioxepin-3(5H)4'-piperidine]hydrochloride 
• 50366-32-0 2-[bis(p-fluorophenyl)-methoxy]ethylamine 

Relevant articles and documents

A Novel Fluorescent Analog of the Dopamine Reuptake Inhibitor GBR12909

Abstract: Dopamine transporter is a transmembrane protein associated with regulation of dopaminergic signal transmission by dopamine reuptake from the synaptic cleft back into cytosol. Some neurological disorders, for example Parkinson’s disease, are characterized by dopaminergic neuron degeneration resulting in dopamine level decrease in synapses. Therefore, dopamine transporter may be considered as a potential target in therapy of neurodegenerative disorders. However, the development of molecular tools based on dopamine transporter inhibitors remains challenging, as there is a lack of knowledge about dopamine transporter regulation and distribution in the brain. The sets of tropane and piperazine derivatives synthesized previously are the most common compounds among a number of dopamine reuptake inhibitors. It should be noted that the highest affinity and selectivity to dopamine transporter (compared with serotonin and norepinephrine ones) were demonstrated by an N-substituted piperazine derivative GBR12909. As GBR12909 has high affinity and selectivity, its structure may serve as a base for the development of novel functionalized derivatives. Design of a new fluorescent derivative based on the structure of dopamine transporter antagonist GBR12909 to investigate the transporter localization and dynamics in presynaptic membrane is the aim of this paper. We synthesized a novel fluorescent analog of dopamine transporter derivative GBR12909 labeled by the BODIPY-FL fluorophore. In order to synthesize this compound, a module synthesis scheme was developed. According to this scheme, the basic scaffold contains a linker fragment with protected amino group on the distal end of the molecule. Such scheme allows us to synthesize a set of variable GBR12909 derivatives through conjugation of various functionally significant fragments at the amino group. The first step of the target compound synthesis includes production of 1-(2-(bis(4-fluorophenyl)methoxy)ethyl)piperazine and tert-butyl(6-((4-(3-iodopropyl)phenyl)amino)-6-oxohexyl)carbamate) followed by their ‘assembly’ into one molecule. After the deprotection of the amino group, it was acylated by fluorescent BODIPY-FL-C3 acid. The fluorescent analog was used to investigate its internalization in an experiment with the PC12 pheochromocytoma cells expressing dopamine transporter. Specific accumulation of the fluorescent analog by the cells via the dopamine transporter was demonstrated, the transporter was rather sensitive to GBR12909 inhibition.

4-phenylsulfonamidopiperidines as calcium channel blockers

The invention relates to piperidinyl compounds of Formula (I): or a pharmaceutically acceptable salt, prodrug, or solvate thereof, wherein R1-R3 and Z are defined as set forth in the specification. The invention is also directed to an assay useful for identifying such compounds as N-type calcium channel modulators or blockers. The invention is also directed to the compounds of Formula (I) and compounds identified by the above assay, and the use of such compounds to treat, prevent or ameliorate a disorder responsive to the blockade of calcium channels, and particularly N-type calcium channels. Compounds of the present invention are especially useful for treating pain.

Scale-up synthesis of the dopamine uptake inhibitor GBR-12909

1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazine (GBR-12909) is a dopamine uptake inhibitor. The development of a robust process for the preparation of this compound in kilogram quantities is described. The primary aims of the development work were to eliminate chromatographic purifications, to minimize the use of environmentally unacceptable reagents, and to improve the overall yield of the three-step convergent process. These objectives were met, with significant improvements obtained in the key coupling reaction of N-(3-phenylpropyl)piperazine dihydrochloride salt with 1-[bis(4-fluorophenyl)methoxy]-2-chloroethane, which was previously low-yielding and lacking in reproducibility.