83154-97-6

Basic information

• Product Name: acetic acid, 2-chloro-, 2,4-dinitrophenyl ester
• Synonyms: 2,4-Dinitrophenyl chloroacetate
• CAS NO: 83154-97-6
• Molecular Formula: C₈H₅ClN₂O₆
• Molecular Weight: 260.5881
• Mol File: 83154-97-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 400.901°C at 760 mmHg
• Flash Point: 196.258°C
• Density: 1.607g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.601
• CAS DataBase Reference: acetic acid, 2-chloro-, 2,4-dinitrophenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: acetic acid, 2-chloro-, 2,4-dinitrophenyl ester(83154-97-6)
• EPA Substance Registry System: acetic acid, 2-chloro-, 2,4-dinitrophenyl ester(83154-97-6)

Safety Data

• Hazardous Substances Data: 83154-97-6(Hazardous Substances Data)

Upstream product

• 51-28-5 2,4-Dinitrophenol 
• 75-57-0 tetramethlyammonium chloride 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 51-28-5 2,4-Dinitrophenol 
• 79-11-8 chloroacetic acid 

Relevant articles and documents

Electron-withdrawing substituents decrease the electrophilicity of the carbonyl carbon. An investigation with the aid of 13C NMR chemical shifts, v(C=O) frequency values, charge densities, and isodesmic reactions to interprete substituent effects on reactivity

13C NMR chemical shifts and v(C=O) frequencies have been measured for several series of phenyl-or acyl-substituted phenyl acetates and for acyl-substituted methyl acetates to investigate the substituent-induced changes in the electrophilic character of the carbonyl carbon. Charge density, bond order, and energy calculations have also been performed. The spectroscopic and charge density results indicate that opposite to the conventional thinking, electron-withdrawing substituents do not increase the electrophilicity of the carbonyl carbon but instead decrease it. On the other hand, reaction energies of the isodesmic reactions designed show that electron-withdrawing substituents destabilize the carbonyl derivatives investigated. So, a significant ground-state destabilization of carboxylic acid esters, and carbonyl compounds in general, due to the decreased resonance stabilization, is proposed as a novel concept to explain both the increase in their reactivity and the changes in the chemical shifts and carbonyl frequencies induced by electron-withdrawing substituents.