38144-19-3

Basic information

• Product Name: Benzoic acid, 3,5-dinitro-, 4-chlorophenyl ester
• Synonyms: Benzoic acid, 3,5-dinitro-, 4-chlorophenyl ester
• CAS NO: 38144-19-3
• Molecular Formula: C₁₃H₇ClN₂O₆
• Molecular Weight: 322.65748
• Mol File: 38144-19-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzoic acid, 3,5-dinitro-, 4-chlorophenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 3,5-dinitro-, 4-chlorophenyl ester(38144-19-3)
• EPA Substance Registry System: Benzoic acid, 3,5-dinitro-, 4-chlorophenyl ester(38144-19-3)

Safety Data

• Hazardous Substances Data: 38144-19-3(Hazardous Substances Data)

Upstream product

• 106-48-9 4-chloro-phenol 
• 99-33-2 3,5-dinitrobenoyl chloride 
• 99-34-3 3,5-dinitrobenzoic acid 
• 1523-21-3 4-nitrophenyl 3,5-dinitrobenzoate 
• 24573-38-4 4-chlorophenolate 

Downstream Products

• 99-34-3 3,5-dinitrobenzoic acid 
• 24573-38-4 4-chlorophenolate 

Relevant articles and documents

Kinetics of the reaction of 4-nitrophenyl benzoates with 4-chlorophenol in the presence of potassium carbonate in dimethylformamide

The effect of the substituent in the benzoyl group on the relative rate and activation parameters of transesterification of substituted 4-nitrophenyl benzoates with 4-chlorophenol in dimethylformamide in the presence of potassium carbonate was studied by the competing reaction technique. The whole series of benzoates showed the enthalpy-entropy compensation effect. 4-Nitrophenyl benzoates having electronacceptor substituents give rise to isokinetic relationship with an isokinetic temperature β of 382 K. The mechanism of the transesterification process is discussed. Pleiades Publishing, Inc., 2006.

Evidence of a stepwise acyl-transfer reaction mechanism: Nonlinear hammett plots for reactions of p-nitrophenyl substituted benzoates with hydroxide and p-chlorophenoxide

The Hammett plots obtained for the title-reactions exhibit a break, i.e. ρ acyl values decrease from 2.21 ~ 2.44 to 1.45 ~ 1.52 as the acyl substituent becomes a strong electron withdrawing group (σ > 0.6). Such a break in the Hammett plots is suggestive of a change in the reaction mechanism and strong evidence of a stepwise mechanism for the acyl-transfer reaction.