7221-31-0

Basic information

• Product Name: 2-(4-NITRO-PHENYLAMINO)-BENZOIC ACID
• Synonyms: 2-(4-NITRO-PHENYLAMINO)-BENZOIC ACID;N-(4-NITROPHENYL)ANTHRANILIC ACID;2-(4-Nitroanilino)benzoic acid
• CAS NO: 7221-31-0
• Molecular Formula: C₁₃H₁₀N₂O₄
• Molecular Weight: 258.2295
• Product Categories: pharmacetical
• Mol File: 7221-31-0.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 465.5°Cat760mmHg
• Flash Point: 235.3°C
• Appearance: /
• Density: 1.435g/cm³
• Vapor Pressure: 1.83E-09mmHg at 25°C
• Refractive Index: 1.694
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(4-NITRO-PHENYLAMINO)-BENZOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-NITRO-PHENYLAMINO)-BENZOIC ACID(7221-31-0)
• EPA Substance Registry System: 2-(4-NITRO-PHENYLAMINO)-BENZOIC ACID(7221-31-0)

Safety Data

• Hazardous Substances Data: 7221-31-0(Hazardous Substances Data)

Usage

General Description

2-(4-NITRO-PHENYLAMINO)-BENZOIC ACID is a chemical compound with the molecular formula C13H10N2O4. It belongs to the class of benzoic acids and is commonly used in the synthesis of pharmaceuticals, dyes, and pigments. The compound has a nitro group and an amino group attached to a benzene ring, making it an important building block in organic chemistry. 2-(4-NITRO-PHENYLAMINO)-BENZOIC ACID has various industrial applications, including as an intermediate in the production of active pharmaceutical ingredients and as a dye intermediate. It is important to handle this chemical with care, as it can pose health hazards if not properly managed.

InChI:InChI=1/C13H10N2O4/c16-13(17)11-3-1-2-4-12(11)14-9-5-7-10(8-6-9)15(18)19/h1-8,14H,(H,16,17)

Upstream product

• 118-92-3 anthranilic acid 
• 100-00-5 4-chlorobenzonitrile 
• 586-78-7 para-nitrophenyl bromide 
• 100-01-6 4-nitro-aniline 
• 118-91-2 ortho-chlorobenzoic acid 
• 88-65-3 2-bromobenzoic-acid 
• 88-67-5 2-Iodobenzoic acid 
• 17763-70-1 methyl 2-(trifluoromethylsulfonyloxy)benzoate 
• 1570135-37-3 N-(2-(4,5-dihydrooxazol-2-yl)phenyl)-2-((4-nitrophenyl)amino)benzamide 

Downstream Products

• 7251-00-5 2-nitroacridone 
• 41139-95-1 N-(p-aminophenyl)anthranilic acid 
• 78938-55-3 2-(4-Nitro-phenylamino)-benzoic acid 2-[(E)-2,4-dioxo-imidazolidin-1-ylimino]-ethyl ester 
• 95216-61-8 2-(4-nitrophenylamino)benzamide 
• 95216-44-7 1-(4-aminophenyl)-2-isopropyl-4(1H)-quinazolinone 
• 70368-48-8 2-Isopropyl-1-(4-nitro-phenyl)-1H-quinazolin-4-one 
• 95216-41-4 2-Cyclopropyl-1-(4-nitro-phenyl)-1H-quinazolin-4-one 
• 95216-43-6 2-cyclobutyl-1-(4-nitrophenyl)-4(1H)-quinazolinone 
• 27918-14-5 2-aminoacridone 
• 581-28-2 2-aminoacridine 
• 1415651-14-7 C₂₁H₁₇N₃O₅ 
• 1415651-19-2 C₂₃H₂₀ClN₃O₅ 
• 1415651-24-9 4-acetamidophenyl-2-[{2-(nitrooxy)ethyl}(4-nitrophenyl)amino]benzoate 

Relevant articles and documents

Light-Driven Intramolecular C?N Cross-Coupling via a Long-Lived Photoactive Photoisomer Complex

Reported herein is a visible-light-driven intramolecular C?N cross-coupling reaction under mild reaction conditions (metal- and photocatalyst-free, at room temperature) via a long-lived photoactive photoisomer complex. This strategy was used to rapidly prepare the N-substituted polycyclic quinazolinone derivatives with a broad substrate scope (>50 examples) and further exploited to synthesize the natural products tryptanthrin, rutaecarpine, and their analogues. The success of gram-scale synthesis and solar-driven transformation, as well as promising tumor-suppressing biological activity, proves the potential of this strategy for practical applications. Mechanistic investigations, including control experiments, DFT calculations, UV-vis spectroscopy, EPR, and X-ray single-crystal structure of the key intermediate, provides insight into the mechanism.

Synthesis and investigation of anti-inflammatory activity of novel nitric oxide donating hybrid drugs

A small library of nitric oxide donating groups, 4-acetamidophenyl-2-[{2- (nitrooxy)ethyl}(phenyl) amino]benzoate (5a-e) possessing a variety of substituents (-H, -NO2, -CH3, -acetamidophenyl, -SO 2NH2) attached to the fourth position of phenyl ring were synthesized and evaluated for anti-inflammatory, analgesic and ulcerogenic potential. Structure-activity relationship data showed that the 2-phenylaminobenzoic acid skeleton is required for selective COX-2 inhibition. Among all compounds 4-acetamidophenyl-2-[{2-(nitrooxy)ethyl}(phenyl)amino] benzoate (5a) has shown potent anti-inflammatory activity while 4-acetamidophenyl-2-[{4-{(4-acetamidophenoxy)carbonyl} phenyl}{2-(nitrooxy) ethyl}amino]benzoate (5d) has shown potent analgesic activity compared to standard drug diclofenac.

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.