15269-50-8

Basic information

• Product Name: 1-(4-Methoxybenzoyl)aziridine
• Synonyms: 1-(4-Methoxybenzoyl)aziridine
• CAS NO: 15269-50-8
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.2
• Mol File: 15269-50-8.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 330.8°C at 760 mmHg
• Flash Point: 153.9°C
• Appearance: /
• Density: 1.219g/cm³
• Vapor Pressure: 0.000162mmHg at 25°C
• Refractive Index: 1.591
• CAS DataBase Reference: 1-(4-Methoxybenzoyl)aziridine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-Methoxybenzoyl)aziridine(15269-50-8)
• EPA Substance Registry System: 1-(4-Methoxybenzoyl)aziridine(15269-50-8)

Safety Data

• Hazardous Substances Data: 15269-50-8(Hazardous Substances Data)

Usage

Chemical structure

A heterocyclic organic compound with a three-membered ring containing one nitrogen atom and two carbon atoms.

Derivation

Derived from aziridine and 4-methoxybenzoyl chloride.

Application

Used in organic synthesis as a reagent for the selective modification of amino acids and peptides.

Potential use

Development of pharmaceuticals and agrochemicals due to its ability to form stable complexes with a variety of nucleophiles.

Biological activity

Studied for its potential antitumor and antimicrobial activities.

Field of interest

Compound of interest in the field of medicinal chemistry.

InChI:InChI=1/C10H11NO2/c1-13-9-4-2-8(3-5-9)10(12)11-6-7-11/h2-5H,6-7H2,1H3

Upstream product

• 151-56-4 ethyleneimine 
• 100-07-2 4-methoxy-benzoyl chloride 

Downstream Products

• 151-56-4 ethyleneimine 
• 536-45-8 sodium anisate 
• 57728-69-5 N-(2-hydroxyethyl)-p-methoxybenzamide 
• 88328-87-4 4-Methoxy-N-(2-methoxy-ethyl)-benzamide 

Relevant articles and documents

Effect of Distortion on the Hydrolytic Reactivity of Amides. 2. N-Pyramidalization: Decomposition of N-Benzoylaziridines in Aqueous Media

The decomposition of para-substituted N-benzoylaziridines (H, OCH3, NO2, Br) in buffered aqueous media is studied at 25 deg C as a function of pH in order to assess the effect of N-pyramidalization on the hydrolytic reactivity of the amide bond.Overall, the reaction shows three dominant terms: OH- and H2O attack on the neutral form and H2O attack on the protonated form of the amide.In base, the exclusive reaction is rate-limiting and irreversible attack of OH- on the C=O unit leading to normal hydrolytic products.This is shown by the first-order dependence on -> from pH 8 to 14 of the hydrolysis rate and by the fact that ca. 50percent 18O-enriched amide recovered from the hydrolysis medium as a function of time shows no 18O loss.Relative to N,N-dimethylbenzamide (kOH-25 deg C = 6.0 * 10-6 M-1 s-1), N-benzoylaziridine is ca. 200 000-fold more susceptible to OH- attack (kOH-25 deg C = 1.1 M-1 s-1).The kOH- terms follow a ?ρ relationship with ρ = 1.68.In acid, the products are not the expected hydrolytic ones of benzoic acid and aziridine.Rather, exclusive ring opening occurs to give p-X-C6H4C(=O)NHCH2CH2OX.In acetate buffers, product analysis by 1H NMR indicates that the ring-opened material consists of alcohol and acetate (X = H and C(=O)CH3).