16124-69-9

Basic information

• Product Name: 4-[(4-nitrophenyl)amino]benzoic acid
• CAS NO: 16124-69-9
• Molecular Formula: C₁₃H₁₀N₂O₄
• Molecular Weight: 258.2295
• Mol File: 16124-69-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 489.2°C at 760 mmHg
• Flash Point: 249.7°C
• Density: 1.435g/cm³
• Vapor Pressure: 2.19E-10mmHg at 25°C
• Refractive Index: 1.694
• CAS DataBase Reference: 4-[(4-nitrophenyl)amino]benzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-[(4-nitrophenyl)amino]benzoic acid(16124-69-9)
• EPA Substance Registry System: 4-[(4-nitrophenyl)amino]benzoic acid(16124-69-9)

Safety Data

• Hazardous Substances Data: 16124-69-9(Hazardous Substances Data)

Usage

General Description

4-[(4-nitrophenyl)amino]benzoic acid is a chemical compound with the molecular formula C13H10N2O4. It is a derivative of benzoic acid and contains a nitrophenylamine group. 4-[(4-nitrophenyl)amino]benzoic acid is often used as a building block in the synthesis of various pharmaceuticals and organic compounds. It has potential applications in the field of medicine and research, particularly in the development of new drugs and biologically active molecules. 4-[(4-nitrophenyl)amino]benzoic acid is also known for its fluorescent properties, which makes it suitable for use as a labeling agent in biological and chemical assays. Overall, it is a versatile chemical with a range of potential applications in various industries.

Upstream product

• 150-13-0 4-amino-benzoic acid 
• 350-46-9 4-Fluoronitrobenzene 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 600170-74-9 4-[(4-nitrophenyl)amino]-N-pyrid-3-ylbenzamide 

Relevant articles and documents

Development of potent and selective inhibitors of aldo-keto reductase 1C3 (type 5 17β-hydroxysteroid dehydrogenase) based on N -phenyl-aminobenzoates and their structure-activity relationships

Aldo-keto reductase 1C3 (AKR1C3; type 5 17β-hydroxysteroid dehydrogenase) is overexpressed in castration resistant prostate cancer (CRPC) and is implicated in the intratumoral biosynthesis of testosterone and 5α-dihydrotestosterone. Selective AKR1C3 inhibitors are required because compounds should not inhibit the highly related AKR1C1 and AKR1C2 isoforms which are involved in the inactivation of 5α-dihydrotestosterone. NSAIDs, N-phenylanthranilates in particular, are potent but nonselective AKR1C3 inhibitors. Using flufenamic acid, 2-{[3-(trifluoromethyl)phenyl]amino}benzoic acid, as lead compound, five classes of structural analogues were synthesized and evaluated for AKR1C3 inhibitory potency and selectivity. Structure-activity relationship (SAR) studies revealed that a meta-carboxylic acid group relative to the amine conferred pronounced AKR1C3 selectivity without loss of potency, while electron withdrawing groups on the phenylamino B-ring were optimal for AKR1C3 inhibition. Lead compounds did not inhibit COX-1 or COX-2 but blocked the AKR1C3 mediated production of testosterone in LNCaP-AKR1C3 cells. These compounds offer promising leads toward new therapeutics for CRPC.

NITROSO DERIVATIVES OF DIPHENYLAMINE

The invention relates to a compound of the formula (I) in which: - R1 represents, independently of each other, a halogen atom; an aliphatic hydrocarbon-based group optionally substituted and/or optionally interrupted by one or more oxygen or sulfur atoms; a nitro group; a cyano group; an amino group; a mono- or dialkylamino group; an alkylcarbonyl group; a carboxyl group; an alkylcarbonylamino group; an alkylsulfonyl group; - R2 represents, independently of each other, a cyano group; a hydroxyl group, an alkylcarbonyl group; a carboxyl group; an alkoxycarbonyl group; an unsubstituted amide group; or a linear or branched alkyl group substituted by a cyano, hydroxyl, carboxyl, alkoxycarbonyl or unsubstituted amide group; - i and j independently being 1 to 5, with the exclusion of the compound for which i and j = 1 and R1 = carboxyl and R2 = alkoxycarbonyl or R1 = CF3 and R2 = carboxyl, and also the pharmaceutically acceptable derivatives, salts, solvates and stereoisomers thereof, including mixtures thereof in all proportions.