6358-23-2

Basic information

• Product Name: 2-(2,4-dinitroanilino)phenol
• Synonyms: 2-(2,4-dinitroanilino)phenol;Phenol, o-(2,4-dinitroanilino).
• CAS NO: 6358-23-2
• Molecular Formula: C₁₂H₉N₃O₅
• Molecular Weight: 275.21696
• Mol File: 6358-23-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 435.4°C at 760 mmHg
• Flash Point: 217.1°C
• Appearance: /
• Density: 1.549g/cm³
• Vapor Pressure: 3.44E-08mmHg at 25°C
• Refractive Index: 1.726
• Stability: Stable. Incompatible with strong oxidizing agents.
• CAS DataBase Reference: 2-(2,4-dinitroanilino)phenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,4-dinitroanilino)phenol(6358-23-2)
• EPA Substance Registry System: 2-(2,4-dinitroanilino)phenol(6358-23-2)

Safety Data

• Hazardous Substances Data: 6358-23-2(Hazardous Substances Data)

Usage

Chemical Properties

orange crystalline powder

General Description

Orange crystals.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

2-(2,4-dinitroanilino)phenol is an organonitrate/phenol. Organonitrate compounds range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. The aromatic nitro compounds may explode in the presence of a base such as sodium hydroxide or potassium hydroxide even in the presence of water or organic solvents. The explosive tendencies of aromatic nitro compounds are increased by the presence of multiple nitro groups. Phenols do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has Ka = 1.3 x 10^[-10]). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases.

Fire Hazard

Flash point data are not available for 2-(2,4-dinitroanilino)phenol, but 2-(2,4-dinitroanilino)phenol is probably combustible.

InChI:InChI=1/C12H9N3O5/c16-12-4-2-1-3-10(12)13-9-6-5-8(14(17)18)7-11(9)15(19)20/h1-7,13,16H

Upstream product

• 110-86-1 pyridine 
• 2363-32-8 2,4-dinitro-2'-aminodiphenyl ether 
• 64-17-5 ethanol 
• 584-48-5 2,4-dinitrobromobenzene 
• 95-55-6 2-amino-phenol 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 100719-20-8 2-[(2-hydroxyphenylamino)methylene]malonic acid diethyl ester 
• 18226-27-2 N-<2-Hydroxy-phenyl>-2,4-dinitro-benzolsulfonamid 
• 7732-18-5 water 
• 70-34-8 2,4-Dinitrofluorobenzene 
• 4185-69-7 1-(2,4-dinitrophenyl)-pyridinium chloride 
• 90-04-0 2-methoxy-phenylamine 
• 14038-08-5 N-(2,4-Dinitrophenyl)-2-methoxy-aniline 

Downstream Products

• 67684-92-8 (2-ethoxy-phenyl)-(2,4-dinitro-phenyl)-amine 
• 62276-07-7 [2-(2,4-dinitro-phenoxy)-phenyl]-(2,4-dinitro-phenyl)-amine 
• 96602-91-4 2-[2-Amino-4-imino-cyclohexa-2,5-dien-(Z)-ylideneamino]-phenol 
• 77279-88-0 4-nitro-2-amino-2'-hydroxy-diphenylamine 
• 50736-54-4 [3-(2,4-dinitro-phenyl)-3H-benzooxazol-2-ylidene]-trifluoromethyl-amine 

Relevant articles and documents

Synthesis and Anti-Staphylococcal Activity of 2,4-Disubstituted Diphenylamines

Infections caused by Staphylococcus aureus are ubiquitous and life threatening. Evolution of resistant strains has necessitated the need to continuously discover new drugs to combat such organisms. Diphenyl ethers, such as triclosan, have recently shown potential as antibacterial agents. In this study, a series of diphenyl amines were synthesized and evaluated for in vitro antibacterial activity against Gram-positive (Staphylococcus aureus, Bacillus subtilis, Staphylococcus epidermidis) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa, Pseudomonas putida) bacteria. Preliminary results showed that six of the twelve synthesized molecules were active against Staphylococcus aureus. Most notable amongst them were compounds 2(2,4-dinitrophenylamino) phenol and 2(2-dinitrophenylamino)phenol having minimum inhibitory concentration (MIC) in the range of 7.8-15.6 μg mL-1 and 7.8-62.5 μg mL-1 respectively for all the eight selected organisms. Five active compounds from the preliminary results were further screened against resistant S. aureus cultures where compounds 2(2,4-dinitrophenylamino)phenol, 2(2-dinitrophenylamino)phenol and 2-chloro-N-(2-(2,4-dichlorophenylamino)phenyl)acetamide gave encouraging results having MIC in the range 3.9-7.8 μg mL-1 for most of the organisms. Results obtained above for the selected organisms and the resistant S. aureus strains conclude that hydroxyl group at 2-position of ring B potentiates the antibacterial activity and overcomes the antibiotic resistance.

SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF SOME 3-OXO-3H-PYRIDOPHENOXAZINE-2-CARBOXYLIC ACIDS

Reaction of ethyl 1,4-dihydro-8-hydroxy-4-oxo-3-quinolinecarboxylates XIIIa - XIIIc with 2,4-dinitrochlorobenzene in N,N-dimethylformamide in the presence of sodium hydrogen carbonate yields appropriate ethyl 3-oxo-3H-pyridophenoxazine-2-carboxylates XIVa - XIVc.Similar reaction of XIIIa and XIIIb in aqueous solution yields mixtures of the respective ester (XIVa and XIVb, respectively) and acid (XIVd and XIVe, respectively).Compounds XIVg - XIVj were prepared by usual methods.The compounds prepared were tested for their antimicrobial activity in vitro.