72566-27-9

Basic information

• Product Name: 1-(2,3-Epoxypropyl)-4-phenylpiperazine
• Synonyms: 1-(2,3-Epoxypropyl)-4-phenylpiperazine
• CAS NO: 72566-27-9
• Molecular Formula: C₁₃H₁₈N₂O
• Molecular Weight: 218.29
• Product Categories: pharmacetical
• Mol File: 72566-27-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 341.8°C at 760 mmHg
• Flash Point: 104.1°C
• Appearance: /
• Density: 1.144g/cm³
• Vapor Pressure: 7.83E-05mmHg at 25°C
• Refractive Index: 1.58
• CAS DataBase Reference: 1-(2,3-Epoxypropyl)-4-phenylpiperazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2,3-Epoxypropyl)-4-phenylpiperazine(72566-27-9)
• EPA Substance Registry System: 1-(2,3-Epoxypropyl)-4-phenylpiperazine(72566-27-9)

Safety Data

• Hazardous Substances Data: 72566-27-9(Hazardous Substances Data)

Usage

General Description

1-(2,3-Epoxypropyl)-4-phenylpiperazine, also known as 4-Phenyl-1-(2,3-epoxypropyl)piperazine, is a chemical compound with potential pharmaceutical and industrial applications. It is a piperazine derivative that contains an epoxy group and a phenyl ring. 1-(2,3-Epoxypropyl)-4-phenylpiperazine has been studied for its potential use in the development of antihypertensive and antipsychotic drugs, as well as its applications in the synthesis of specialty chemicals and polymers. It has also been investigated for its cytotoxic and anticancer properties, and has been used as a precursor in the production of epoxy resins and other industrial materials. The compound's unique structure and properties make it a promising candidate for further research and development in both the pharmaceutical and industrial sectors.

InChI:InChI=1/C13H18N2O/c1-2-4-12(5-3-1)15-8-6-14(7-9-15)10-13-11-16-13/h1-5,13H,6-11H2

Upstream product

• 92-54-6 4-phenyl-1-piperazine 
• 106-89-8 epichlorohydrin 
• 67568-57-4 3-<4-Phenylpiperazinyl>-2-hydroxypropyl chloride 

Downstream Products

• 1360748-75-9 1-(2-(7-chloroquinolin-4-ylamino)ethylamino)-3-(4-phenylpiperazin-1-yl)propan-2-ol 
• 1360748-91-9 3-(2-(7-chloroquinolin-4-ylamino)ethyl)-5-((4-phenylpiperazin-1-yl)methyl)oxazolidin-2-one 
• 17692-31-8 dropropizine 
• 1313518-13-6 7-(4-phenylpiperazino)-7,8-dihydro-6H-[1,3]oxazino[2,3-f]theophylline 
• 91595-86-7 4,5-dihydro-5--2-oxazolamine 
• 72722-92-0 1-ethyl-5-[2-hydroxy-3-(4-phenyl-piperazin-1-yl)-propoxy]-3,4-dihydro-1H-quinolin-2-one 

Relevant articles and documents

Catalytic, Kinetic, and Mechanistic Insights into the Fixation of CO2 with Epoxides Catalyzed by Phenol-Functionalized Phosphonium Salts

A series of hydroxy-functionalized phosphonium salts were studied as bifunctional catalysts for the conversion of CO2 with epoxides under mild and solvent-free conditions. The reaction in the presence of a phenol-based phosphonium iodide proceeded via a first order rection kinetic with respect to the substrate. Notably, in contrast to the aliphatic analogue, the phenol-based catalyst showed no product inhibition. The temperature dependence of the reaction rate was investigated, and the activation energy for the model reaction was determined from an Arrhenius-plot (Ea=39.6 kJ mol?1). The substrate scope was also evaluated. Under the optimized reaction conditions, 20 terminal epoxides were converted at room temperature to the corresponding cyclic carbonates, which were isolated in yields up to 99 %. The reaction is easily scalable and was performed on a scale up to 50 g substrate. Moreover, this method was applied in the synthesis of the antitussive agent dropropizine starting from epichlorohydrin and phenylpiperazine. Furthermore, DFT calculations were performed to rationalize the mechanism and the high efficiency of the phenol-based phosphonium iodide catalyst. The calculation confirmed the activation of the epoxide via hydrogen bonding for the iodide salt, which facilitates the ring-opening step. Notably, the effective Gibbs energy barrier regarding this step is 97 kJ mol?1 for the bromide and 72 kJ mol?1 for the iodide salt, which explains the difference in activity.

Synthesis of Aminoquinoline-Based Aminoalcohols and Oxazolidinones and Their Antiplasmodial Activity

Novel aminoquinoline β-aminoalcohol and oxazolidinone derivatives were designed, synthesized, and evaluated for in vitro antiplasmodial activity against a chloroquine-sensitive (3D7) and chloroquine-resistant (K1) strains of Plasmodium falciparum. A few β-aminoalcohol derivatives were more potent than chloroquine against chloroquine-sensetive Plasmodiums. The potency of these derivatives decreased against chloroquine-resistant species in all cases (higher resistance indices), suggesting a possible cross-resistance between this group of compounds and chloroquine which could be due to their structural similarity. Although changing β-aminoalcohols to their oxazolidinone counterparts decreased the potency in all the cases, the compounds were still active and the resistance indices for these compounds improved significantly in comparison with those of β-aminoalcohols. This may indicate the absence of cross-resistance between these new derivatives and chloroquine.