5442-46-6

Basic information

• Product Name: 4-methoxy-2-nitro-N-phenylaniline
• Synonyms: benzenamine, 4-methoxy-2-nitro-N-phenyl-
• CAS NO: 5442-46-6
• Molecular Formula: C₁₃H₁₂N₂O₃
• Molecular Weight: 244.246
• Mol File: 5442-46-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 397°C at 760 mmHg
• Flash Point: 193.9°C
• Density: 1.276g/cm³
• Vapor Pressure: 1.64E-06mmHg at 25°C
• Refractive Index: 1.639
• CAS DataBase Reference: 4-methoxy-2-nitro-N-phenylaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-methoxy-2-nitro-N-phenylaniline(5442-46-6)
• EPA Substance Registry System: 4-methoxy-2-nitro-N-phenylaniline(5442-46-6)

Safety Data

• Hazardous Substances Data: 5442-46-6(Hazardous Substances Data)

Upstream product

• 96-96-8 4-methoxy-2-nitroaniline 
• 5344-78-5 4-bromo-3-nitroanizole 
• 62-53-3 aniline 
• 591-50-4 iodobenzene 

Downstream Products

• 68765-55-9 4-methoxy-N₁-phenylbenzene-1,2-diamine 
• 2876-18-8 2-methoxyphenazine 
• 4190-95-8 2-hydroxyphenazine 
• 250691-78-2 5-methoxy-1-phenylbenzimidazole hydrochloride 

Relevant articles and documents

Identification of a Novel Oxadiazole Inhibitor of Mammalian Target of Rapamycin

We performed a biochemical screen against mTOR using in-house small molecule library. Two novel, structurally distinct hits were identified. Among them, a novel oxadiazole scaffold compound (2) suppressed the phosphorylation of both S6K1 and Akt1 in HeLa cells. Docking study suggested that 2 is ATP-competitive and shows a pi-pi interaction with Trp2239 and hydrogen bonds with Trp2239 and Thr2245. Through derivatization, a slightly more potent analogue (2a) was identified with IC50 of 9.6 μM. Our study provides a starting point for discovery of novel potent mTOR inhibitors.

Efficient methods for the synthesis of 2-hydroxyphenazine based on the Pd-catalyzed N-arylation of aryl bromides

(Chemical Equation Presented) Substituted diphenylamines can be synthesized by Pd(0)-catalyzed N-arylation using o-nitroanilines and nitro-substituted aryl bromides for a substrate. Cyclization of the diphenylamines by various methods, including the intramolecular Pd(0)-catalyzed N-arylation, produces 2-methoxyphenazine which can easily be deprotected to give 2-hydroxyphenazine. This phenazine is required to synthesize methanophenazine, a novel redoxactive cofactor isolated from methanogenic archaea.