136367-45-8

Basic information

• Product Name: 2-chloro-4-nitrophenyl 3,5-dinitrobenzoate
• Synonyms: 2-chloro-4-nitrophenyl 3,5-dinitrobenzoate
• CAS NO: 136367-45-8
• Molecular Weight: 367.659
• Mol File: 136367-45-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-chloro-4-nitrophenyl 3,5-dinitrobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-4-nitrophenyl 3,5-dinitrobenzoate(136367-45-8)
• EPA Substance Registry System: 2-chloro-4-nitrophenyl 3,5-dinitrobenzoate(136367-45-8)

Safety Data

• Hazardous Substances Data: 136367-45-8(Hazardous Substances Data)

Upstream product

• 619-08-9 2-chloro-4-nitrophenol 
• 99-33-2 3,5-dinitrobenoyl chloride 

Downstream Products

• 2900-63-2 3,5-dinitrobenzohydrazide 
• 619-08-9 2-chloro-4-nitrophenol 
• 1037569-82-6 N-[N-(3,5-dinitro-benzoyl)-glycyl]-glycine 
• 57499-86-2 1-(3,5-dinitro-benzoyl)-piperidine 

Relevant articles and documents

Kinetic study on nucleophilic displacement reactions of 2-chloro-4-nitrophenyl x-substituted-benzoates with primary amines: Reaction mechanism and origin of the a-effect

Second-order rate constants for aminolysis of 2-chloro-4-nitrophenyl X-substituted-benzoates (1a-h) have been measured spectrophotometrically in 80 mol % H2O/20 mol % DMSO at 25.0 °C. The Bronsted-type plot for the reactions of 2-chloro-4-nitrophenyl benzoate (1d) with a series of primary amines curves downward, which has been taken as evidence for a stepwise mechanism with a change in rate-determining step (RDS). The Hammett plots for the reactions of 1a-h with hydrazine and glycylglycine are nonlinear while the Yukawa- Tsuno plots exhibit excellent linearity with ρX = 1.22-1.35 and r = 0.57-0.59, indicating that the nonlinear Hammett plots are not due to a change in RDS but are caused by stabilization of substrates possessing an electron-donating group (EDG) through resonance interactions between the EDG and C=O bond of the substrates. The α-effect exhibited by hydrazine increases as the substituent X changes from a strong EDG to a strong electron-withdrawing group (EWG). It has been concluded that destabilization of hydrazine through the electronic repulsion between the adjacent nonbonding electrons is not solely responsible for the substituent dependent α-effect but stabilization of the transition state is also a plausible origin of the α-effect.

Kinetic study on aminolysis of 2-chloro-4-nitrophenyl x-substituted-benzoates in acetonitrile and in H2O Containing 20mol% DMSO: Effects of medium and substituent X on reactivity and reaction mechanism

Second-order rate constants for reactions of 2-chloro-4-nitrophenyl X-substituted-benzoates 1a-1j with a series of cyclic secondary amines in MeCN have been measured. Comparison of the kinetic results with those reported previously for the corresponding reactions carried out in H2O containing 20 mol % DMSO has revealed that amines are less reactive in MeCN. The Bronsted-type plot for the aminolysis of 2-chloro-4-nitrophenyl benzoate (1f) in MeCN is linear with βnuc= 0.64, which is in contrast to the curved Bronsted-type plot reported for the reaction performed in the H2O-DMSO misxture. The Hammett plot for the reactions of 1a-1j with piperidine consists of two intersecting straight lines while the Yukawa-Tsuno plot exhibits an excellent linear correlation with ρX= 1.22 and r = 0.60, indicating that the nonlinear Hammett plot is not due to a change in rate-determining step but is caused by stabilization of substrates possessing an electron-donating substituent through resonance interactions between the substituent and the carbonyl functionality. It has been concluded that medium change from the H2O-DMSO mixture to MeCN forces the aminolysis of 1a-1j to proceed through a concerted mechanism by destabilizing the zwitterionic tetrahedral intermediate (T±).