16292-86-7

Basic information

• Product Name: 5-amino-2-nitrophenol
• Synonyms: 5-Amino-2-nitrophenol; phenol, 5-amino-2-nitro-
• CAS NO: 16292-86-7
• Molecular Formula: C₆H₆N₂O₃
• Molecular Weight: 154.1234
• Mol File: 16292-86-7.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 350.5°C at 760 mmHg
• Flash Point: 165.8°C
• Density: 1.511g/cm³
• Vapor Pressure: 2.16E-05mmHg at 25°C
• Refractive Index: 1.688
• CAS DataBase Reference: 5-amino-2-nitrophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-amino-2-nitrophenol(16292-86-7)
• EPA Substance Registry System: 5-amino-2-nitrophenol(16292-86-7)

Safety Data

• Hazardous Substances Data: 16292-86-7(Hazardous Substances Data)

Upstream product

• 119-76-6 N,N'-(4-nitro-m-phenylene)-bis-acetamide 
• 952016-85-2 5-acetylamino-2-nitro-benzenesulfonic acid 
• 81946-00-1 3-Butyl-7-chloro-6-nitro-3H-quinazolin-4-one 
• 53449-14-2 7-chloro-6-nitro-4(3H)-quinazolinone 
• 329-71-5 2,5-dinitrophenol 
• 5131-58-8 2,4-diaminonitrobenzene 
• 6317-89-1 3-acetamidophenyl acetate 
• 66136-64-9 acetic acid-(3-amino-4-nitro-anilide) 
• 825-41-2 3-chloro-4-nitroaniline 

Downstream Products

• 611-07-4 5-chloro-2-nitrophenol 
• 807640-27-3 benzoic acid, 4-fluoro-,5-[(4-fluorobenzoyl)amino]-2-nitrophenyl ester 
• 807640-28-4 benzamide,4-fluoro-N-(3-hydroxy-4-nitrophenyl)- 
• 807640-29-5 benzamide, N-[3-[[6-(acetyloxy)hexyl]oxy]-4-nitrophenyl]-4-fluoro- 

Relevant articles and documents

A probable hydrogen-bonded meisenheimer complex: An unusually high S NAr reactivity of nitroaniline derivatives with hydroxide ion in aqueous media

Observations show that nitroanilines exhibit an unusually high S NAr reactivity with OH- in aqueous media in reactions that produce nitrophenols. SNAr reaction of 4-nitroaniline (2a) in aqueous NaOH for 16 h yields 4-nitrophenol (4a) quantitatively, whereas a similar reaction of 4-nitrochlorobenzene (1a) gave 4a in 2% yield together with recovered 1a in 97%, suggesting that the leaving ability of the NH2 group far surpasses that of Cl under these conditions. An essential feature of SNAr reactions of nitroanilines is probably that the NH2 leaving group participates in a hydrogen-bonding interaction with H 2O. Density functional theory (DFT) calculations for a set of 4-nitroaniline, OH-, and H2O suggest a possible formation of a Meisenheimer complex stabilized by hydrogen-bonding interactions and a six-membered ring structure. The results obtained here contrast with conventional SNAr reactivity profiles in which nitroanilines are nearly unreactive with nucleophiles in organic solvents.

A convenient method to aniline compounds using microwave-assisted transfer hydrogenation

The reduction of mononitro and dinitro aromatic compounds to their aniline analogues using microwave-assisted transfer hydrogenation has been demonstrated. The optimised conditions used, with some examples, are described herein. Georg Thieme Verlag Stuttgart.