1523-15-5

Basic information

• Product Name: 2,4-dinitrophenyl benzoate
• Synonyms: 2,4-Dinitrophenyl benzoate; phenol, 2,4-dinitro-, benzoate (ester)
• CAS NO: 1523-15-5
• Molecular Formula: C₁₃H₈N₂O₆
• Molecular Weight: 288.2124
• Mol File: 1523-15-5.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 499°C at 760 mmHg
• Flash Point: 234.6°C
• Density: 1.466g/cm³
• Vapor Pressure: 4.31E-10mmHg at 25°C
• Refractive Index: 1.642
• CAS DataBase Reference: 2,4-dinitrophenyl benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-dinitrophenyl benzoate(1523-15-5)
• EPA Substance Registry System: 2,4-dinitrophenyl benzoate(1523-15-5)

Safety Data

• Hazardous Substances Data: 1523-15-5(Hazardous Substances Data)

Usage

General Description

2,4-dinitrophenyl benzoate is a chemical compound with the molecular formula C13H9N3O5. It is a yellow, crystalline compound that is commonly used in organic chemistry as a reagent for the identification and characterization of alcohols, phenols, and carboxylic acids. When treated with an alcohol or phenol, 2,4-dinitrophenyl benzoate forms a colored precipitate, which can be used to determine the presence and structure of the original alcohol or phenol. This reaction is known as the 2,4-dinitrophenylhydrazine test, and it is a widely used method in organic chemistry for the analysis of unknown organic compounds.

Upstream product

• 51-28-5 2,4-Dinitrophenol 
• 94-36-0 dibenzoyl peroxide 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 65116-92-9 Benzil-α-anti(CO)- 
• 20255-22-5 lithium salt of 2,4-dinitrophenol 
• 1011-73-0 sodium 2,4-dinitrophenoxide 
• 14314-69-3 potassium 2,4-dinitrophenolate 
• 582-25-2 Potassium benzoate 
• 97-00-7 1-chloro-2,4-dinitro-benzene 

Downstream Products

• 5874-58-8 N-(benzoyl)-L-proline 
• 2901-80-6 N-benzoyl-D,L-valine 
• 495-69-2 Hippuric Acid 
• 16513-72-7 4-cyanophenyl benzoate 
• 1523-17-7 4-bromophenyl benzoate 
• 614-32-4 3-methylphenyl benzoate 
• 614-34-6 p-cresyl benzoate 
• 1523-19-9 4-methoxyphenyl benzoate 
• 1523-13-3 3-nitrophenyl benzoate 
• 404947-48-4 (4-allylhepta-1,6-dien-4-yl) benzene 
• 93-99-2 benzoic acid phenyl ester 
• 14314-69-3 potassium 2,4-dinitrophenolate 
• 2005-08-5 4-chlorophenyl benzoate 
• 959-22-8 p-nitrophenylbenzoate 

Relevant articles and documents

Ph3P-I2 mediated aryl esterification with a mechanistic insight

In order to better understand the reaction mechanism and to obtain optimal conditions, the Ph3P-I2/Et3N mediated aryl esterification reaction was thoroughly investigated. Using a specific reagent addition sequence, the reaction proceeds remarkably well especially with acidic substrates. 31P NMR studies revealed that the formation of an aryloxyphosphonium salt is crucial in governing the reaction path toward the formation of phenolic esters.

Hydrolysis of 1-(X-substituted-benzoyl)-4-aminopyridinium ions: Effect of substituent X on reactivity and reaction mechanism

A kinetic study is reported for hydrolysis of 1-(X-substituted-benzoyl)-4- aminopyridinium ions 2a-i, which were generated in situ from the nucleophilic substitution reaction of 2,4-dinitrophenyl X-substituted-benzoates 1a-i with 4-aminopyridine in 80 mol% H2O/20 mol% DMSO at 25.0 ± 0.1 °C. The plots of pseudo-first-order rate constants kobsdvs. pyridine concentration are linear with a large positive intercept, indicating that the hydrolysis of 2a-i proceeds through pyridine-catalyzed and uncatalyzed pathways with the rate constant kcat and ko, respectively. The Hammett plots for kcat and ko consist of two intersecting straight lines, which might be taken as evidence for a change in the rate-determining step (RDS). However, it has been proposed that the nonlinear Hammett plots are not due to a change in the RDS but are caused by stabilization of 2a-i in the ground state through a resonance interaction between the π-electron-donor substituent X and the carbonyl functionality. This is because the corresponding Yukawa-Tsuno plots exhibit excellent linear correlations with ρX = 1.45 and r = 0.76 for kcat while ρX = 1.39 and r = 0.72 for ko. A possibility that the hydrolysis of 2a-i proceeds through a concerted mechanism has been ruled out on the basis of the large ρX values. Thus, the reaction has been concluded to proceed through a stepwise mechanism in which the leaving group departs after the RDS since OH- is more basic and a poorer nucleofuge than 4-aminopyridine. The Royal Society of Chemistry 2011.

Nonlinear Hammett plots in pyridinolysis of 2,4-dinitrophenyl X-substituted benzoates: Change in RDS versus resonance contribution

Second-order rate constants (kOH-) have been measured for nucleophilic substitution reactions of 2,4-dinitrophenyl X-substituted benzoates (1a-j) with Z-substituted pyridines in 80 mol% H2O/20 mol% DMSO at 25.0 ± 0.1 °C. The Hammett plots for the reactions of 1a-j with pyridines consist of two intersecting straight lines, i.e., a large ρ value for the reactions of substrates (1a-c) possessing an electron-donating group (EDG) in the benzoyl moiety and a small one for substrates (1e-j) bearing an electron-withdrawing group (EWG). The nonlinear Hammett plots have been attributed to stabilization of the ground state of substrates 1a-c through resonance interactions between the electron-donating substituent and the carbonyl functionality, since the corresponding Yukawa-Tsuno plots exhibit excellent linear correlations with large r values. It has been shown that substrates 1e-j are not unusually more reactive than would be expected from the Hammett substituent constants, but rather, substrates 1a-c exhibit lower reactivity than would be predicted. The Bronsted-type plots for pyridinolysis of 1a-j are linear with βnuc = 0.74-0.98, indicating that the reaction proceeds through a stepwise mechanism in which the second step is the RDS. It has been concluded that the electronic nature of the substituent X in the benzoyl moiety does not influence the RDS, but the degree of bond formation (or the effective charge on the nucleophilic site) in the transition state becomes more significant as the substituent X changes from a strong EDG to a strong EWG.