18292-63-2

Basic information

• Product Name: 1-(p-bromobenzoyl)aziridine
• Synonyms: 1-(p-bromobenzoyl)aziridine
• CAS NO: 18292-63-2
• Molecular Weight: 226.073
• Mol File: 18292-63-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1-(p-bromobenzoyl)aziridine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(p-bromobenzoyl)aziridine(18292-63-2)
• EPA Substance Registry System: 1-(p-bromobenzoyl)aziridine(18292-63-2)

Safety Data

• Hazardous Substances Data: 18292-63-2(Hazardous Substances Data)

Usage

General Description

1-(p-bromobenzoyl)aziridine, also known as p-bromobenzoylaziridine, is a chemical compound with the molecular formula C10H8BrNO. It is a reactive aziridine derivative with a bromobenzoyl substituent attached to the aziridine ring. 1-(p-bromobenzoyl)aziridine is commonly used in organic synthesis and as a building block for the preparation of various pharmaceuticals and agrochemicals. It is a versatile reagent in the formation of carbon-carbon and carbon-nitrogen bonds in the synthesis of complex organic molecules. Additionally, 1-(p-bromobenzoyl)aziridine has been studied for its potential applications in the field of materials science due to its unique reactivity and structural properties. It should be handled with caution and in accordance with appropriate safety protocols due to its potential for toxicity and reactivity.

Upstream product

• 151-56-4 ethyleneimine 
• 586-75-4 4-chlorobenzoyl chloride 

Downstream Products

• 95086-95-6 N-(2-methoxyethyl)-p-bromobenzamide 
• 151-56-4 ethyleneimine 
• 2532-15-2 sodium 4-bromobenzoate 
• 57728-67-3 N-(2-hydroxyethyl)-p-bromobenzamide 
• 189120-01-2 2-(4-bromo-phenyl)-4,5-dihydro-oxazole 

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).