22525-95-7

Basic information

• Product Name: 2'-(Oxiranylmethoxy)-3-phenylpropiophenon
• Synonyms: Einecs 245-052-7;2-(2,3-Epoxypropoxy)-3-phenylpropylophenone;Propafenone IMp. C (EP);Propafenone IMpurity C (EP/BP/USP);1-[2-(oxiran-2-ylMethoxy)phenyl]-3-phenylpropan-1-one;Propafenone EP Impurity C;2'-(2,3-EPOXYPROPOXY)-3-PHENYLPROPLOPHENONE;2'-(oxiranylmethoxy)-3-phenylpropiophenone
• CAS NO: 22525-95-7
• Molecular Formula: C₁₈H₁₈O₃
• Molecular Weight: 282.33
• EINECS: 245-052-7
• Product Categories: Aromatics;Heterocycles
• Mol File: 22525-95-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 56-58°C
• Boiling Point: 452.8 °C at 760 mmHg
• Flash Point: 219.6 °C
• Appearance: Pale-yellow solid
• Density: 1.164 g/cm³
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Ethyl Acetate, DMSO (Slightly)
• CAS DataBase Reference: 2'-(Oxiranylmethoxy)-3-phenylpropiophenon(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-(Oxiranylmethoxy)-3-phenylpropiophenon(22525-95-7)
• EPA Substance Registry System: 2'-(Oxiranylmethoxy)-3-phenylpropiophenon(22525-95-7)

Safety Data

• Hazardous Substances Data: 22525-95-7(Hazardous Substances Data)

Usage

Description

2'-(Oxiranylmethoxy)-3-phenylpropiophenon, also known as Propafenone EP Impurity C, is an organic compound that is characterized as a pale-yellow solid. It is an impurity found in the synthesis of propafenone (P757500), a medication used to treat certain types of heart rhythm disorders.

Uses

Used in Pharmaceutical Industry:
2'-(Oxiranylmethoxy)-3-phenylpropiophenon is used as an impurity in the synthesis of propafenone (P757500) for the pharmaceutical industry. Its presence is significant as it can impact the quality and efficacy of the final drug product. Ensuring the removal or reduction of this impurity is crucial for maintaining the safety and effectiveness of propafenone as a medication for heart rhythm disorders.
Additionally, understanding the properties and behavior of this impurity can aid in the development of improved synthesis methods or purification techniques, which could potentially enhance the overall quality of propafenone and other related pharmaceutical compounds.

Upstream product

• 1214-47-7 1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one 
• 16619-51-5 2'-allyloxychalcone 
• 106-89-8 epichlorohydrin 
• 100-52-7 benzaldehyde 
• 118-93-4 o-hydroxyacetophenone 
• 3516-95-8 2'-hydroxy-3-phenylpropiophenone 

Downstream Products

• 34183-22-7 propafenone hydrochloride 
• 86382-78-7 C₂₉H₃₃NO₄*ClH 
• 22568-59-8 1-(2-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)-3-phenylpropan-1-one 
• 1341229-08-0 C₂₉H₃₂N₂O₄*ClH 
• 1341228-46-3 C₂₇H₃₁NO₃*ClH 
• 184043-22-9 C₂₉H₃₄N₂O₄*ClH 
• 1341228-50-9 C₃₀H₄₁NO₃*ClH 
• 34183-26-1 C₂₂H₂₉NO₃*ClH 

Relevant articles and documents

Chemoselective Hydrosilylation of the α,β-Site Double Bond in α,β- And α,β,γ,δ-Unsaturated Ketones Catalyzed by Macrosteric Borane Promoted by Hexafluoro-2-propanol

The B(C6F5)3-catalyzed chemoselective hydrosilylation of α,β- and α,β,γ,δ-unsaturated ketones into the corresponding non-symmetric ketones in mild reaction conditions is developed. Nearly 55 substrates including those bearing reducible functional groups such as alkynyl, alkenyl, cyano, and aromatic heterocycles are chemoselectively hydrosilylated in good to excellent yields. Isotope-labeling studies revealed that hexafluoro-2-propanol also served as a hydrogen source in the process.

Optimization of propafenone analogues as antimalarial leads

Propafenone, a class Ic antiarrythmic drug, inhibits growth of cultured Plasmodium falciparum. While the drug's potency is significant, further development of propafenone as an antimalarial would require divorcing the antimalarial and cardiac activities as well as improving the pharmacokinetic profile of the drug. A small array of propafenone analogues was designed and synthesized to address the cardiac ion channel and PK liabilities. Testing of this array revealed potent inhibitors of the 3D7 (drug sensitive) and K1 (drug resistant) strains of P. falciparum that possessed significantly reduced ion channel effects and improved metabolic stability. Propafenone analogues are unusual among antimalarial leads in that they are more potent against the multidrug resistant K1 strain of P. falciparum compared to the 3D7 strain.

Structure-activity relationship studies on benzofuran analogs of propafenone-type modulators of tumor cell multidrug resistance

A series of benzofurylethanolamine analogs of propafenone (1a) have been prepared and evaluated for multidrug resistance-reversing activity in two in vitro assay systems. As for propafenones, an excellent correlation of biological data with calculated lipophilicity values was found for benzofurans, whereby the latter generally had lower activity/lipophilicity ratios. Almost identical slopes of the regression lines were obtained for both propafenones and benzofurans. Multiple linear regression analysis of the complete data set yielded an equation with excellent predictive power (r2(cross-valid) = 0.968). Interaction measurements with artificial membranes indicated that the differences in activity between these two series of compounds are not due to differences in the interaction pattern with biological membranes.