619-18-1

Basic information

• Product Name: 2,5-Dinitroaniline
• Synonyms: 2,5-Dinitroaniline
• CAS NO: 619-18-1
• Molecular Formula: C₆H₅N₃O₄
• Molecular Weight: 183.1216
• Mol File: 619-18-1.mol

Chemical Properties

• Melting Point: 138°C
• Boiling Point: 316.77°C (rough estimate)
• Flash Point: 196.7°C
• Appearance: /
• Density: 1.6188 (rough estimate)
• Vapor Pressure: 1.16E-06mmHg at 25°C
• Refractive Index: 1.6910 (estimate)
• PKA: -2.20±0.10(Predicted)
• CAS DataBase Reference: 2,5-Dinitroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dinitroaniline(619-18-1)
• EPA Substance Registry System: 2,5-Dinitroaniline(619-18-1)

Safety Data

• Hazardous Substances Data: 619-18-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H5N3O4/c7-5-3-4(8(10)11)1-2-6(5)9(12)13/h1-3H,7H2

Upstream product

• 619-16-9 1-chloro-2,5-dinitrobenzene 
• 7664-41-7 ammonia 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 122-28-1 N-(3-nitrophenyl)acetanilide 
• 7664-93-9 sulfuric acid 
• 3717-73-5 2,5-dinitroacetanilide 
• 60956-27-6 N-(2,3-dinitrophenyl)acetamide 
• 329-71-5 2,5-dinitrophenol 
• 57-13-6 urea 
• 602-03-9 2,3-dinitroaniline 

Downstream Products

• 61149-61-9 N,N-dimethyl-2,5-dinitro-aniline 
• 343855-35-6 2-iodo-1,4-dinitro-benzene 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 148533-73-7 5-nitro-2-(pyridine-4-yl)-1H-benzo[d]imidazole 
• 3694-52-8 2,3-diamino-nitrobenzene 
• 17801-99-9 1,4-dichloro-2-methoxy-5-nitrobenzene 
• 119-21-1 1-chloro-2,4-dimethoxy-5-nitrobenzene 
• 97-50-7 5-chloro-2,4-dimethoxyaniline 
• 4920-79-0 2-chloro-4-nitroanisole 
• 17488-25-4 1,4-dichloro-2,5-dinitrobenzene 

Relevant articles and documents

Steric-Hindrance-Induced Regio- and Chemoselective Oxidation of Aromatic Amines

Unusual regio- and chemoselective oxidation of aromatic amines hindered with ortho substituents (except -NH2, -NHCH3, and -OH) to the corresponding nitro compounds is described by use of nonanebis(peroxoic acid). The mechanistic investigation for selective oxidation of amines ortho-substituted with -NH2 or -OH showed the involvement of H-bonding between the ortho hydrogen of the adjacent -XH group (where X = NH, NR, or O) and an oxygen atom from the diperoxy acid. Various mono- and diamines are oxidized into corresponding mononitro derivatives in high yield and purity without employing any protection strategies. The protocol was also found to successful on the gram scale.

Copper-catalyzed amination of aryl halides with aqueous ammonia under mild conditions

A Cu(I) generated in situ from CuSO4·5H 2O/sodium ascorbate catalyzed cross-coupling reaction of aryl halides with aqueous ammonia for the synthesis of primary aromatic amines has been developed. Key to the success included the application of aqueous ammonia under a homogeneous condition. A Cu(I) generated in situ from CuSO4· 5H2O/sodium ascorbate catalyzed cross-coupling reaction of aryl halides with aqueous ammonia for the synsthesis of primary aromatic amines has been developed. Key to the success included the application of aqueous ammonia under a homogeneous condition.

The Rearragement of Aromatic Nitro Compounds. Part 1. The Reactions of Nitroanilines in Aqueous Sulphuric Acid

A number of substituted 2-nitroanilines rearange in concentrated sulphuric acid at 110 deg C to yield products that appear to be derived from 1,3-migration of the 2-nitro-group.For 2,3-dinitroaniline, the rate of reaction is almost independent of acidity over the range 83-97percent sulphuric acid and the solvent isotope effect k(H2SO4)/k(D2SO4) is 1.3-1.9.Methyl and t-butyl groups, when present as additional substituents in 2,3-dinitroaniline, have only a small effect on the reaction rate but 3-methyl-2-nitroaniline reacts much more slowly than 2,3-dinitroaniline.These results are discussed in terms of a rate-determining migration of the 2-nitro group following protonation at the 2-position.

A Comparison of the Reactions of Some Ethyl N-Arylcarbamates with Those of the Corresponding Acetanilides. I. Nitration

The reactions of some ethyl N-arylcarbamates and of the corresponding acetanilides towards 1 equiv. of sodium nitrate in concentrated sulfuric acid at 0-5 deg have been compared with one another and have been found to exhibit significant differences.Except in the case of the unsubstituted analogues, nitration of the carbamates was found to occur significantly more quickly than that of the acetanilides as shown by (i) a representative competitive nitration, and (ii) the fact the carbamates containing a nitro group are nitrated smoothly whereas the corresponding nitroacetanilides are slow to react.On the basis of competitive reactions, it is suggested that this difference in reactivity is due to steric factors.

Water-soluble trisazo 8-amino-naphthol-1 dyes

Very effective direct dyeing of cotton and other hydroxyl- or nitrogen-containing fibers is effected with water-soluble triasazo dyes having the formula: where A is a radical of a diazoconstituent and A3 is a radical of a coupling constituent STR1 and A1 or A2 or both can have their azo linkages reversed. These dyes are very fast particularly to washing and to perspiration, and are so effective with cotton that dye baths for such use are rapidly exhausted and the disposal of used bath is less of a problem.