203860-01-9

Basic information

• Product Name: 1-(3,4-Difluorobenzyl)piperazine 2HCl
• Synonyms: 1-(3,4-Difluorobenzyl)piperazine 2HCl;1-[(3,4-difluorophenyl)methyl]piperazine
• CAS NO: 203860-01-9
• Molecular Formula: C₁₁H₁₄F₂N₂
• Molecular Weight: 285.1609464
• Mol File: 203860-01-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(3,4-Difluorobenzyl)piperazine 2HCl(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3,4-Difluorobenzyl)piperazine 2HCl(203860-01-9)
• EPA Substance Registry System: 1-(3,4-Difluorobenzyl)piperazine 2HCl(203860-01-9)

Safety Data

• Hazardous Substances Data: 203860-01-9(Hazardous Substances Data)

Usage

Description

1-(3,4-Difluorobenzyl)piperazine 2HCl is a chemical compound that features a piperazine ring with a 3,4-difluorobenzyl group attached to it, along with two hydrochloride (HCl) groups. 1-(3,4-Difluorobenzyl)piperazine 2HCl is recognized for its potential applications in medicinal chemistry due to the presence of the 3,4-difluorobenzyl group, which is known to confer unique and often enhanced pharmacological properties to fluorinated compounds. The addition of hydrochloride groups improves the water solubility of the compound, facilitating its use in laboratory settings. As such, 1-(3,4-Difluorobenzyl)piperazine 2HCl is a versatile intermediate in pharmaceutical production and organic synthesis, with promising implications in drug discovery and development.

Uses

Used in Pharmaceutical Industry:
1-(3,4-Difluorobenzyl)piperazine 2HCl serves as an intermediate in the production of pharmaceuticals, leveraging its unique structural features to contribute to the development of new medications. The presence of the 3,4-difluorobenzyl group can enhance the pharmacological profile of resulting drugs, potentially improving their efficacy, selectivity, and other therapeutic properties.
Used in Organic Synthesis:
As a precursor in organic synthesis, 1-(3,4-Difluorobenzyl)piperazine 2HCl is utilized to synthesize a variety of complex organic compounds. Its structural components allow for the creation of diverse chemical entities, which can be further modified or used as building blocks in the synthesis of advanced organic molecules.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 1-(3,4-Difluorobenzyl)piperazine 2HCl is employed as a research tool to explore the effects of fluorination on the properties of drug candidates. Its use can lead to a better understanding of how fluorinated compounds interact with biological targets, potentially resulting in the discovery of more effective and safer medications.
Used in Laboratory Settings:
Due to its increased water solubility, 1-(3,4-Difluorobenzyl)piperazine 2HCl is easier to handle in laboratory environments. This makes it a preferred choice for researchers working on projects that require the synthesis or manipulation of chemical compounds with improved solubility properties.

Upstream product

• 110-85-0 piperazine 
• 85118-01-0 alpha-bromo-3,4-difluorotoluene 
• 1393441-76-3 C₁₆H₂₂F₂N₂O₂ 

Relevant articles and documents

Flavonoid derivatives as selective ABCC1 modulators: Synthesis and functional characterization

A series of chromones, bearing substituted amino groups or N-substituted carboxamide moieties in position 2, was synthesized and characterized in cellular assays for modulation of the ABC transporters ABCC1 (MDCKII-MRP1 cells), ABCB1 (Kb-V1 cells) and ABCG2 (MCF-7/Topo cells). The most potent ABCC1 modulators identified among these flavonoid-type compounds were comparable to the reference compound reversan regarding potency, but superior in terms of selectivity concerning ABCB1 and ABCG2 (2-[4-(Benzo[c][1,2,5]oxadiazol-5-ylmethyl)piperazin-1-yl]-5,7-dimethoxy-4H-chromen-4-one (51): ABCC1, IC50 11.3-1/4M; inactive at ABCB1 and ABCG2). Compound 51 was as effective as reversan in reverting ABCC1-mediated resistance to cytostatics in MDCKII-MRP1 cells and proved to be stable in mouse plasma and cell culture medium. Modulators, such as compound 51, are of potential value as pharmacological tools for the investigation of the (patho)physiological role of ABCC1.

Discovery of novel protease activated receptors 1 antagonists with potent antithrombotic activity in vivo

Protease activated receptors (PARs) or thrombin receptors constitute a class of G-protein-coupled receptors (GPCRs) implicated in the activation of many physiological mechanisms. Thus, thrombin activates many cell types such as vascular smooth muscle cells, leukocytes, endothelial cells, and platelets via activation of these receptors. In humans, thrombin-induced platelet aggregation is mediated by one subtype of these receptors, termed PAR1. This article describes the discovery of new antagonists of these receptors and more specifically two compounds: 2-[5-oxo-5-(4-pyridin-2-ylpiperazin-1-yl)penta-1,3- dienyl]benzonitrile 36 (F 16618) and 3-(2-chlorophenyl)-1-[4-(4-fluorobenzyl) piperazin-1-yl]propenone 39 (F 16357), obtained after optimization. Both compounds are able to inhibit SFLLR-induced human platelet aggregation and display antithrombotic activity in an arteriovenous shunt model in the rat after iv or oral administration. Furthermore, these compounds are devoid of bleeding side effects often observed with other types of antiplatelet drugs, which constitutes a promising advantage for this new class of antithrombotic agents. 2009 American Chemical Society.