3460-11-5

Basic information

• Product Name: 4-NITROBENZANILIDE
• Synonyms: P-NITROBENZANILIDE;N-(4-NITROBENZOYL)ANILINE;4-Nitro-N-phenylbenzamide;N-Phenyl-4-nitrobenzamide
• CAS NO: 3460-11-5
• Molecular Formula: C13H10N2O3
• Molecular Weight: 242.23
• EINECS: 222-403-2
• Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 3460-11-5.mol
• Article Data: 147

Chemical Properties

• Boiling Point: 339.4°Cat760mmHg
• Flash Point: 159.1°C
• Appearance: /
• Density: 1.344g/cm³
• Vapor Pressure: 9.19E-05mmHg at 25°C
• Refractive Index: 1.671
• CAS DataBase Reference: 4-NITROBENZANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-NITROBENZANILIDE(3460-11-5)
• EPA Substance Registry System: 4-NITROBENZANILIDE(3460-11-5)

Safety Data

• Hazardous Substances Data: 3460-11-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 3327, 1974 DOI: 10.1021/jo00937a004

InChI:InChI=1/C13H10N2O3/c16-13(14-11-4-2-1-3-5-11)10-6-8-12(9-7-10)15(17)18/h1-9H,(H,14,16)

Upstream product

• 5466-84-2 4-nitrophthalic anhydride 
• 62-53-3 aniline 
• 555-16-8 4-nitrobenzaldehdye 
• 1227476-15-4 Azobenzene 
• 1429-05-6 phenyl 4-nitrobenzoate 
• 13733-21-6 (4-nitro-benzoyl)-carbamic acid ethyl ester 
• 62-23-7 4-nitro-benzoic acid 
• 5326-10-3 phosphoric acid trianilide 
• 587-14-4 N,N'-diphenylsulfamide 
• 18440-21-6 2,4-bis(anilino)-1,3-diphenyl-1,3,2,4-diazadiphosphetidine 
• 3128-43-6 S-phenyl 4-nitrobenzothioate 
• 6631-86-3 S-(p-chlorophenyl) p-nitrothiobenzoate 
• 28122-84-1 4-nitrothiobenzoic acid S-p-tolyl ester 
• 69737-96-8 S-(p-nitrophenyl) p-nitrothiobenzoate 

Downstream Products

• 84570-81-0 2-(4-nitrophenyl)-4-phenylquinazoline 
• 619-73-8 4-nitrobenzyl chloride 
• 10359-18-9 N-(4-nitrobenzyl)aniline 
• 62-53-3 aniline 
• 876893-22-0 N-[(1H-1,2,3-benzotriazol-1-yl)(4-nitrophenyl)methylidene]-N-phenylamine 
• 14213-27-5 1-phenyl-5-(4-nitrophenyl)-1H-tetrazole 
• 14121-97-2 4-hydroxybenzanilide 
• 4270-58-0 4-hydroxy-N-phenylbenzothioamide 
• 13432-43-4 4-methoxy-N-phenyl-thiobenzimidic acid methyl ester 
• 3054-31-7 4-amino-thiobenzoic acid anilide 
• 26060-23-1 4-methoxy-N-phenylthiobenzamide 
• 4389-05-3 4-amino-N-(4-sulfamoylphenyl)benzamide 
• 346719-87-7 N-(4-nitro-benzoyl)-sulfanilic acid acetylamide 
• 619-80-7 4-nitrobenzamide 

Relevant articles and documents

Amidation of aryl halides catalyzed by silica-supported bidentate phosphine palladium complex

A silica-supported bidentate phosphine palladium complex was prepared from poly-4-oxa-6,7-bis(diphenylphosphino)heptyl siloxane and palladium chloride in acetone. It was an efficient catalyst for the amidation of aryl halides with carbon monoxide and aniline at 1 atm pressure, affording aryl amides.

Cyclic hydroxamic acids as oxygenating agents - Conversion of imines to anilides

Cyclic hydroxamic acid mediated functional group modification of an imine to anilide is reported.

Visible-light-induced direct construction of amide bond from carboxylic acids with amines in aqueous solution

A novel visible-light-promoted N-acylation for the synthesis of amides from easily available carboxylic acids with amines in the presence of I2 within 2.5 h in aqueous solution has been developed. Using sunlight as the visible light source greatly reduces the cost of experiments and produces almost no toxic effects. Hence, this study provides an alternative catalytic system for the construction of a wide range of amides with readily available materials. Moreover, the strategy was successfully applied in the preparation of N-(3-(2,6-dimethoxyphenoxy)-7-nitroquinoxalin-2-yl)benzohydrazide, which displayed a signification anti-proliferation effect on A549, MCF-7 and HCT116 cell lines.

Optimizing the structure of (salicylideneamino)benzoic acids: Towards selective antifungal and anti-staphylococcal agents

An increasing resistance of human pathogenic bacteria and fungi has become a global health problem. Based on previous reports of 4-(salicylideneamino)benzoic acids, we designed, synthesised and evaluated their me-too analogues as potential antimicrobial agents. Forty imines derived from substituted salicylaldehydes and aminobenzoic acids, 4-aminobenzoic acid esters and 4-amino-N-phenylbenzamide were designed using molecular hybridization and prodrug strategies. The target compounds were synthesized with high yields and characterized by spectral methods. They were investigated against a panel of Gram-positive and Gram-negative bacteria, mycobacteria, yeasts and moulds. The most active imines were tested to determine their cytotoxicity and selectivity in HepG2 cells. Dihalogenosalicylaldehydes-based derivatives showed potent broad-spectrum antimicrobial properties, particularly against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (minimum inhibitory concentrations, MIC, from 7.81 μM) and Enterococcus faecalis (MIC of ≥15.62 μM), yeasts (MIC from 7.81 μM) and Trichophyton interdigitale mould (MIC of ≥3.90 μM). Methyl 4-[(2-hydroxy-3,5-diiodobenzylidene)amino]benzoate 4h exhibited excellent in vitro activity along with low toxicity to mammalian cells. This compound is selective for staphylococci, Candida spp. and Trichophyton interdigitale. In addition, this imine was evaluated as a potential inhibitor of Gram-positive biofilms. The successful approach used provided some promising derivatives with more advantageous properties than the parent 4-(salicylideneamino)benzoic acids.