19614-29-0

Basic information

• Product Name: 1-(p-Nitrobenzoyl)aziridine
• Synonyms: 1-(p-Nitrobenzoyl)aziridine
• CAS NO: 19614-29-0
• Molecular Formula: C₉H₈N₂O₃
• Molecular Weight: 192.1714
• Mol File: 19614-29-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 390°Cat760mmHg
• Flash Point: 189.7°C
• Appearance: /
• Density: 1.443g/cm³
• Vapor Pressure: 2.73E-06mmHg at 25°C
• Refractive Index: 1.656
• CAS DataBase Reference: 1-(p-Nitrobenzoyl)aziridine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(p-Nitrobenzoyl)aziridine(19614-29-0)
• EPA Substance Registry System: 1-(p-Nitrobenzoyl)aziridine(19614-29-0)

Safety Data

• Hazardous Substances Data: 19614-29-0(Hazardous Substances Data)

Usage

General Description

1-(p-Nitrobenzoyl)aziridine is a chemical compound with the molecular formula C10H9N3O3. It is a derivative of aziridine, a three-membered heterocyclic compound containing a nitrogen atom. The compound contains a p-nitrobenzoyl group, which is a benzoyl group with a nitro substituent at the para position. 1-(p-Nitrobenzoyl)aziridine is used in organic synthesis and as a reagent in the preparation of various other compounds. It is known to exhibit reactivity and can undergo various chemical reactions, making it a valuable intermediate in the synthesis of complex organic molecules.

InChI:InChI=1/C9H8N2O3/c12-9(10-5-6-10)7-1-3-8(4-2-7)11(13)14/h1-4H,5-6H2

Upstream product

• 151-56-4 ethyleneimine 
• 122-04-3 4-nitro-benzoyl chloride 

Downstream Products

• 7465-63-6 2-(4-Nitrophenyl)-4,5-dihydrooxazole 
• 54998-50-4 4-amino-N-[2-(4-thiazol-2-yl-piperazin-1-yl)-ethyl]-benzamide 
• 95086-97-8 N-(2-methoxyethyl)-p-aminobenzamide 
• 6640-65-9 N-(2-hydroxyethyl)-4-nitrobenzamide 
• 151-56-4 ethyleneimine 
• 3847-57-2 sodium 4-nitrobenzoate 
• 95086-96-7 N-(2-methoxyethyl)-p-nitrobenzamide 
• 5688-33-5 2-Fluor-2-<2-(4-nitro-benzoylamino)-aethyl>-malonsaeure-diaethylester 
• 54998-49-1 4-nitro-N-[2-(4-thiazol-2-yl-piperazin-1-yl)-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).