75112-65-1

Basic information

• Product Name: 2-[(4-nitrophenyl)amino]naphthalene-1,4-dione
• CAS NO: 75112-65-1
• Molecular Formula: C₁₆H₁₀N₂O₄
• Molecular Weight: 294.2616
• Mol File: 75112-65-1.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 500.1°C at 760 mmHg
• Flash Point: 256.3°C
• Density: 1.491g/cm³
• Vapor Pressure: 3.9E-10mmHg at 25°C
• Refractive Index: 1.728
• CAS DataBase Reference: 2-[(4-nitrophenyl)amino]naphthalene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[(4-nitrophenyl)amino]naphthalene-1,4-dione(75112-65-1)
• EPA Substance Registry System: 2-[(4-nitrophenyl)amino]naphthalene-1,4-dione(75112-65-1)

Safety Data

• Hazardous Substances Data: 75112-65-1(Hazardous Substances Data)

Usage

Physical state

Bright yellow powder

Molecular weight

282.26 g/mol

Usage

Manufacturing of dyes, pigments, and pharmaceuticals; organic synthesis; UV-absorbing additive in polymers and plastics

Aromatic structure

Suitable for use in organic synthesis

Nitro group presence

Potential precursor for the synthesis of various organic compounds

Biological activities

Being researched for potential therapeutic agent role

Upstream product

• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 100-01-6 4-nitro-aniline 
• 130-15-4 [1,4]naphthoquinone 
• 110-86-1 pyridine 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 2348-82-5 2-methoxy-1,4-naphthoquinone 
• 6628-97-3 2-(phenylamino)naphthoquinone 

Downstream Products

• 75112-66-2 2-chloro-3-[(4-nitrophenyl)amino]-1,4-naphthoquinone 
• 858020-17-4 2-(4-amino-phenylamino)-1,4-naphthoquinone 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 100-01-6 4-nitro-aniline 

Relevant articles and documents

Synthesis and studies of the antifungal activity of 2-anilino-/2,3-dianilino-/2-phenoxy- and 2,3-diphenoxy-1,4-naphthoquinones

Several synthetic and natural naphthoquinone derivatives have been associated with antifungal activity. Candida albicans is a fungus that is known to exist in the normal human flora, but under certain conditions it can cause mild to fatal infections. Its pathogenicity has been associated with fungus conversion from cellular yeast to filamentous form Y–M. Inhibition of this process by several anilino-, dianilino-, phenoxy-, and diphenoxy-1,4-naphthoquinones was investigated in order to find some correlation between structure, redox properties and biological activity.

General method for the high yield preparation of 2-(4-X-phenylene)amine-1,4-naphthoquinones (X = ferrocenyl, OMe, Me, I, Cl, and NO2) from 2-methoxy-1,4-naphthoquinone and investigation of H+ and Mg2+ catalysts with DFT calculations

A rapid and simple method for the high yield preparation of 2-(4-X-phenylene)amine-1,4-naphthoquinones from 2-methoxy-1,4-naphthoquinone, in boiling MeOH, using MgCl2 and p-toluenesulfonic acid as catalysts is described. This methodology has been applied successfully to the synthesis of electron donor (4-OMe, 4-Me, 4-ferrocenyl) and electron withdrawing (4-I, 4-Cl, 4- and 3-NO2) aniline derivatives. The effect of both H+ and Mg2+ as catalysts was investigated using DFT calculations carried out at the B3LYP/6-31G(d) level. The electronic properties of the novel 2-(4-ferrocenylphenylene)amine-1,4-naphthoquinone 3b were investigated and show that the ferrocenyl and the methoxy group have similar electron donor properties in 2-(4-methoxy)amine-1,4-naphthoquinone 3a.