14985-27-4

Basic information

• Product Name: (2S,3S)-2-(4-methoxyphenyl)-3-(4-nitrophenyl)oxirane
• CAS NO: 14985-27-4
• Molecular Formula: C₁₅H₁₃NO₄
• Molecular Weight: 271.268
• Mol File: 14985-27-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 424°C at 760 mmHg
• Flash Point: 186.6°C
• Density: 1.301g/cm³
• Vapor Pressure: 5.28E-07mmHg at 25°C
• Refractive Index: 1.616
• CAS DataBase Reference: (2S,3S)-2-(4-methoxyphenyl)-3-(4-nitrophenyl)oxirane(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-2-(4-methoxyphenyl)-3-(4-nitrophenyl)oxirane(14985-27-4)
• EPA Substance Registry System: (2S,3S)-2-(4-methoxyphenyl)-3-(4-nitrophenyl)oxirane(14985-27-4)

Safety Data

• Hazardous Substances Data: 14985-27-4(Hazardous Substances Data)

Usage

General Description

(2S,3S)-2-(4-methoxyphenyl)-3-(4-nitrophenyl)oxirane, also known as methoxyphenyl-nitrophenyl oxirane, is a chemical compound with a molecular formula C15H13NO4. It is an epoxide, which is a three-membered cyclic ether with one oxygen atom and two carbon atoms in the ring. (2S,3S)-2-(4-methoxyphenyl)-3-(4-nitrophenyl)oxirane is chiral, meaning it has a non-superimposable mirror image, and the (2S,3S) designation indicates the stereochemistry of the molecule. It is commonly used as a building block in organic synthesis, and it has potential applications in pharmaceuticals and agrochemicals. The presence of the methoxy and nitrophenyl groups in the molecule gives it interesting chemical and biological properties, and it is of interest to researchers in the field of medicinal and synthetic chemistry.

Upstream product

• 41570-69-8 1-(4-nitrobenzyl)-tetrahydrothiophenium bromide 
• 105-13-5 4-Methoxybenzyl alcohol 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 123-11-5 4-methoxy-benzaldehyde 
• 4648-33-3 (E)-1-methoxy-4-(4-nitrostyryl)benzene 
• 4648-14-0 (Z)-1-methoxy-4-[2-(4-nitrophenyl)ethenyl]benzene 

Downstream Products

• 13628-96-1 2-bromo-2-(4-methoxyphenyl)-1-(4-nitrophenyl)ethanone 
• 129913-38-8 Ethyl 5-(p-methoxyphenyl)-2-(p-nitrophenyl)furan-3-carboxylate 
• 129913-37-7 Ethyl 5-(p-methoxyphenyl)-2-(p-nitrophenyl)furan-4-carboxylate 
• 129913-34-4 Dimethyl cis-2-(p-methoxyphenyl)-5-(p-nitrophenyl)-2,5-dihydrofuran-3,4-dicarboxylate 
• 129913-34-4 Dimethyl trans-2-(p-methoxyphenyl)-5-(p-nitrophenyl)-2,5-dihydrofuran-3,4-dicarboxylate 
• 129913-36-6 Dimethyl 2-(p-methoxyphenyl)-5-(p-nitrophenyl)furan-3,4-dicarboxylate 
• 555-16-8 4-nitrobenzaldehdye 
• 123-11-5 4-methoxy-benzaldehyde 
• 106-51-4 p-benzoquinone 
• 107245-95-4 (3R,5S)-3-(4-Methoxy-phenyl)-5-(4-nitro-phenyl)-[1,2,4]trioxolane 

Relevant articles and documents

Visible light-mediated oxidative quenching reaction to electron-rich epoxides: Highly regioselective synthesis of α-bromo (di)ketones and mechanism study

A novel and simple procedure was developed for the regioselective synthesis of α-bromo (di)ketones from electron-rich epoxides via visible light photoredox catalysis. Through optimization of solvent and light source, the reaction can be rapidly achieved under mild conditions. Moreover, the possible reaction mechanism was proposed and further supported by control experiments.

Experimental evidence for multiple oxidation pathways in the (salen)Mn-catalyzed epoxidation of alkenes

The substrate electronic effects on the selectivity in the catalytic epoxidation of para-substituted cis stilbenes 2a-i were investigated by using (R,R)-[N,N′-bis(3,5-di-tBu-salicylidene)-1,2-cyclohexanediamine] manganese(III) chloride 1 in benzene as the catalyst with iodosobenzene as the terminal oxidant. A Hammett study of the selectivity results reveals a stronger electrophilic character than previously assumed in the (salen)Mn-catalyzed reaction. In general, the best correlations with the experimental values were obtained by using the Hammett σ+ values, which gave ρ = -1.37 for the rate of cisepoxide formation and ρ = -0.43 for the rate of the stepwise process leading to the corresponding trans product. The reaction involves two separate pathways as indicated also by the competitive breakdown of the intermediate on the path to trans epoxide for methoxy-substituted substrates. The asynchronicity in the concerted pathway leading to cis epoxide is apparent for 4-methoxy-4′-nitrostilbene, which yields cis epoxide with 75% ee entirely as a result of electronic effects.