35202-08-5

Basic information

• Product Name: 4-(4-nitrophenyl)oxetan-2-one
• CAS NO: 35202-08-5
• Molecular Formula: C₉H₇NO₄
• Molecular Weight: 193.1562
• Mol File: 35202-08-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 382.2°C at 760 mmHg
• Flash Point: 199.9°C
• Density: 1.435g/cm³
• Vapor Pressure: 4.79E-06mmHg at 25°C
• Refractive Index: 1.608
• CAS DataBase Reference: 4-(4-nitrophenyl)oxetan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-nitrophenyl)oxetan-2-one(35202-08-5)
• EPA Substance Registry System: 4-(4-nitrophenyl)oxetan-2-one(35202-08-5)

Safety Data

• Hazardous Substances Data: 35202-08-5(Hazardous Substances Data)

Upstream product

• 57999-52-7 3-Bromo-3-(p-nitrophenyl)propionic acid 
• 108-24-7 acetic anhydride 
• 555-16-8 4-nitrobenzaldehdye 
• 463-51-4 Ketene 
• 127146-25-2 acetic anhydride carbanion 
• 953-26-4 ethyl 4-nitrocinnamate 
• 75-36-5 acetyl chloride 

Downstream Products

• 61960-78-9 1-[3-hydroxy-3-(4-nitro-phenyl)-propionyl]-piperidine 
• 100-13-0 4-nitrostyrene 
• 15719-64-9 methylammonium carbonate 
• 619-89-6 p-nitrocinnamic acid 
• 57999-52-7 3-Bromo-3-(p-nitrophenyl)propionic acid 

Relevant articles and documents

β-LACTONE AS INTERMEDIATE IN THE PERKIN REACTION CATALYZED BY TERTIARY AMINES

The Perkin reaction catalyzed by tertiary amines is found to run not according to the aldol-type condensation mechanism but according to the mechanism in which the first stage is the formation and cycloaddition of ketene, yielding a β-lactone, which cleaves to the unsaturated acid.

A one-pot synthesis of 3-arylglutaric anhydrides by reaction of ketene with aromatic aldehydes and ketones

Aromatic aldehydes and ketones react with ketene under Lewis acid catalysis to produce β-lactones, which in situ react with another molecule of ketene to produce 3-arylglutaric anhydrides. The mechanism, scope, and limitation of this one-pot synthesis of 3-substituted glutaric anhydrides are discussed.

GENERATION AND PROPERTIES OF ACETIC ANHYDRIDE CARBANION

In the reaction between ketene and acetate ions the labile acetic anhydride carbanion is formed.This carbanion generated in situ in the presence of 4-nitrobenzaldehyde undergoes cycloaddition yielding β-lactone and, further, 4-nitrocinnamic acid (Path A).It can also undergo numerous inter- and intramolecular reactions producing various by-products, i.e.CO2, acetoacetic acid (tetrabutylammonium salt), propen-2-ol acetate, acetone, acetylacetone (Path B).Analogical products were obtained with carbanion generated from acetic anhydride by sodium hydride.