1523-20-2

Basic information

• Product Name: Benzoic acid, 3,5-dinitro-, phenyl ester
• Synonyms: Benzoic acid, 3,5-dinitro-, phenyl ester
• CAS NO: 1523-20-2
• Molecular Formula: C₁₃H₈N₂O₆
• Molecular Weight: 288.21242
• Mol File: 1523-20-2.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzoic acid, 3,5-dinitro-, phenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 3,5-dinitro-, phenyl ester(1523-20-2)
• EPA Substance Registry System: Benzoic acid, 3,5-dinitro-, phenyl ester(1523-20-2)

Safety Data

• Hazardous Substances Data: 1523-20-2(Hazardous Substances Data)

Upstream product

• 99-34-3 3,5-dinitrobenzoic acid 
• 98-80-6 phenylboronic acid 
• 591-50-4 iodobenzene 
• 66003-76-7 Diphenyliodonium triflate 
• 610-30-0 2,4-dinitrobenzoic acid 
• 108-95-2 phenol 
• 99-33-2 3,5-dinitrobenoyl chloride 
• 1523-21-3 4-nitrophenyl 3,5-dinitrobenzoate 
• 3229-70-7 phenolate 
• 102-09-0 bis(phenyl) carbonate 
• 139-02-6 sodium phenoxide 

Downstream Products

• 3229-70-7 phenolate 
• 99-34-3 3,5-dinitrobenzoic acid 

Relevant articles and documents

Preparation and use of lithium tritide and lithium trimethoxyborotritide

Two new tritide reducing agents, Li3H and Li(CH3O)3B3H, have been prepared at the carrier-free level and used to reduce 2-naphthaldehyde to tritiated β-naphthalene methanol, to produce C3H3OR, and to synthesize a methyl-tritiated secondary amine.

Development of 3,5-dinitrobenzoate-based 5-lipoxygenase inhibitors

Human 5-lipoxygenase (5-LOX) is a well-validated target for anti-inflammatory therapy. Development of novel 5-LOX inhibitors with higher activities is highly demanded. In previous study, we have built a model for the active conformation of human 5-LOX, and identified naphthalen-1-yl 3,5-dinitrobenzoate (JMC-4) as a 5-LOX inhibitor by virtual screening. In the present work, 3,5-dinitrobenzoate-based 5-lipoxygenase inhibitors were developed. Twenty aryl 3,5-dinitrobenzoates, N-aryl 3,5-dinitrobenzamides and analogues were designed and synthesized. Several of them were found with significantly increased activities according to cell-free assay and human whole blood assay. The structure-activity relationship study may provide useful insights for designing effective 5-LOX inhibitors.

Nucleophilic displacement at the benzoyl centre: A study of the change in geometry at the carbonyl carbon atom

The second-order rate constants for the reaction between hydroxide ion and phenoxide ion with 4-nitrophenyl esters of substituted benzoic acids in 10% acetonitrile-water (v/v) solution obey Hammett σ correlations. The values of the Hammett ρ of 1.67 (κArO) and 2.14 (κOH) are consistent with a large change in hybridization at the central carbon by comparison with the ρ value for a standard reaction where a full sp2 to sp3 change occurs. The transition state for the concerted reaction thus has a substantially tetrahedral geometry. The observation of the anti-Hammond effect whereby the ρ value for the hydroxide ion exceeds that of the less reactive phenoxide ion is consistent with a concerted, ANDN, mechanism for these reactions. A stepwise mechanism, AN + DN, is unlikely to yield a measurable break in the Hammett correlation for a change in the benzoyl substituent if the partitioning of the putative tetrahedral intermediate involves forward and reverse reactions with Hammett correlations possessing similar ρ values.