14401-98-0

Basic information

• Product Name: N-benzyl-3,5-dinitrobenzamide
• Synonyms: N-benzyl-3,5-dinitrobenzamide;BenzaMide, 3,5-dinitro-N-(phenylMethyl)-
• CAS NO: 14401-98-0
• Molecular Formula: C₁₄H₁₁N₃O₅
• Molecular Weight: 301.25424
• Mol File: 14401-98-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-benzyl-3,5-dinitrobenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzyl-3,5-dinitrobenzamide(14401-98-0)
• EPA Substance Registry System: N-benzyl-3,5-dinitrobenzamide(14401-98-0)

Safety Data

• Hazardous Substances Data: 14401-98-0(Hazardous Substances Data)

Upstream product

• 99-34-3 3,5-dinitrobenzoic acid 
• 100-46-9 benzylamine 
• 99-33-2 3,5-dinitrobenoyl chloride 
• 87581-19-9 2,5-dioxopyrrolidin-1-yl 3,5-dinitrobenzoate 

Relevant articles and documents

The Aminolysis of N-Hydroxysuccinimde Esters. A Structure-Reactivity Study

Twelwe amines, which vary substantially in basicity and steric environment around N, have been allowed to compete-in anhydrous dioxane solution-in the aminolysis of the N-hydroxysuccinimide esters of unsubstituted, p-OCH3, p-NO2, and 3,5-(NO2)2 benzoic acids.The amines, which encompass a basicity range of 6.5 pK units, display a 10000-fold variation in reactivity in their reaction with the p-NO2-ester.For the sterically unhindered amines, a Broensted-type plot of log kobsd vs. pKa has a slope of ca. 0.7.The data fit a model (Satterthwait, A.C.; Jenks, W.P.J.Am.Chem.Soc. 1974, 96, 7018-7044) in which reversible formation of a tetrahedral intermediate is followed by rate-determining breakdown to products.Appreciable sensitivity to steric factors, as evidenced from the depressed rates with α-methylbenzylamine and diethylamine, substantiates reversible formation of a crowded tetrahedral intermediate prior to the rate-determining step.The Hammett ρ values for the competitive acylation of aniline, α-methylbenzylamin, and benzylamine by substituted N-succinimidyl benzoates,are 1.4, 1.2, and 1.1, respectively.These values reflect the selectivity expected for these amines, and the substantial accumulation of charge density at the acyl C in the formation of the tetrahedral intermediate.Individual rate constants for the aminolysis of N-succinimidyl p-methoxybenzoate by n-butylamine, and by piperidine, both show first-order and second-order terms in .The general-base catalysis term is suggestive of a path involving proton transfer in the rate-determining step.

Synthesis and biological evaluation of substituted N-alkylphenyl-3,5- dinitrobenzamide analogs as anti-TB agents

Here, a medicinal chemistry study of an N-alkylphenyl-3,5-dinitrobenzamide (DNB) scaffold as a potent anti-TB agent is presented. A series of chemical modifications were performed and forty-three new molecules were synthesized to study the structure-activity relationship (SAR) by evaluating against a sensitive strain (H37Rv) of Mycobacterium tuberculosis (MTB). Potent DNB analogs 4b, 7a, 7c, 7d, 7j, 7r and 9a were further tested against resistant strains of MTB. Their intracellular as well as bactericidal potential was also evaluated. Cytotoxicity and in vivo pharmacokinetic studies suggested that DNB analogs have an acceptable safety index, in vivo stability and bio-availability. From the present work, two compounds 7a and 7d have shown nanomolar to sub micro-molar MIC in extracellular and intracellular assays.