3442-62-4

Basic information

• Product Name: 2-NITROPHENAZINE
• Synonyms: 2-Nitrophenazine
• CAS NO: 3442-62-4
• Molecular Formula: C₁₂H₇N₃O₂
• Molecular Weight: 0
• Mol File: 3442-62-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 447.7°C at 760 mmHg
• Flash Point: 224.6°C
• Appearance: /
• Density: 1.444g/cm³
• Vapor Pressure: 8.7E-08mmHg at 25°C
• Refractive Index: 1.767
• CAS DataBase Reference: 2-NITROPHENAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-NITROPHENAZINE(3442-62-4)
• EPA Substance Registry System: 2-NITROPHENAZINE(3442-62-4)

Safety Data

• Hazardous Substances Data: 3442-62-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H7N3O2/c16-15(17)8-5-6-11-12(7-8)14-10-4-2-1-3-9(10)13-11/h1-7H

Upstream product

• 92-82-0 Phenazin 
• 304-81-4 Phenazin-mono-N-Oxyd 
• 106038-76-0 2,4-Dinitrodiphenylacetamide 

Relevant articles and documents

Pseudomonas fluorescens showing antifungal activity against macrophomina phaseolina, a severe pathogenic fungus of soybean, produces phenazine as the main active metabolite

Pseudomonas fluorescens 9 and Bacillus subtilis 54, proposed as biofungicides to control Macrophomina phaseolina, a dangerous pathogen of soybean and other crops, were grown in vitro to evaluate their ability to produce metabolites with antifungal activity. The aim of the manuscript was to identify the natural compounds responsible for their antifungal activity. Only the culture filtrates of P. fluorescens 9 showed strong antifungal activity against M. phaseolina. Its organic extract contained phenazine and mesaconic acid (1 and 2), whose antifungal activity was tested against M. phaseolina, as well as Cercospora nicotianae and Colletotrichum truncatum, other pathogens of soybean; however, only compound 1 exhibited activity. The antifungal activity of compound 1 was compared to phenazine-1-carboxylic acid (PCA, 3), 2-hydroxyphenazine (2-OH P, 4), and various semisynthetic phenazine nitro derivatives in order to perform a structure–activity relationship (SAR) study. PCA and phenazine exhibited the same percentage of growth inhibition in M. phaseolina and C. truncatum, whereas PCA (3) showed lower activity against C. nicotianae than phenazine. 2-Hydrox-yphenazine (4) showed no antifungal activity against M. phaseolina. The results of the SAR study showed that electron attractor (COOH and NO2) or repulsor (OH) groups significantly affect the antifungal growth, as well as their α-or β-location on the phenazine ring. Both PCA and phenazine could be proposed as biopesticides to control the soybean pathogens M. phaseolina, C. nicotianae, and C. truncatum, and these results should prompt an investigation of their large-scale production and their suitable formulation for greenhouse and field applications.

Photochemical Reaction of 2,4-Dinitrodiphenylacetamide and Related Compounds: Spectroscopic and Chemical Identification of Intermediates

2,4'-Dinitrodiphenylacetamide 1b reacts via the triplet state to give 3-nitrophenazine 5-oxide 2b.The initial step is addition of the nitro group to the C=O bond.This intermediate 7 rearranges in the ms time scale to yield an O-acylnitro derivative 8.This, in turn, undergoes heterocyclic cleavage (rate dependent upon solvent polarity) and the aminium cation thus formed cyclizes to 2b.Intermediate 7 is sensitive to acid-catalysed hydrolysis, and the cleavage of 8 and subsequent cyclization are influenced by various additives.Thus, with triphenylphosphine a phosphoranylidenamino derivative is obtained, and 2,6-di-tert-butylphenol gives 4-nitro-2-nitrosodiphenylamine.Two other amides are compared.