# Dinitroaniline

Dinitroanilines are a class of chemical compounds with the chemical formula C$_6$H$_5$N$_3$O$_4$. They are derived from both aniline and dinitrobenzenes. There are six isomers: 2,3-dinitroaniline, 2,4-dinitroaniline, 2,5-dinitroaniline, 2,6-dinitroaniline, 3,4-dinitroaniline, and 3,5-dinitroaniline.

## Uses

Dinitroanilines are intermediates in the preparation of various industrially important chemicals including dyes and pesticides.
Dinitroaniline herbicides are mostly derived from trifluralin. Dinitroaniline herbicides include benfluralin, butralin, chlornidine, dinitramine, dipropalin, ethalfluralin, fluchloralin, isopropalin, methalpropalin, nitralin, nitrofor, oryzalin, pendimethalin, prodiamine, profluralin, and trifluralin. Trifluralin, pendimethalin and ethalfluralin are the most widely commercially used. Dinitroaniline herbicides generally are 2,6-dinitroanilines, work by inhibiting microtubule formation, have low to moderate human toxicity, high aquatic toxicity and are applied pre-emergently, often to control grasses and broad-leafed weeds.
2,4-Dinitroaniline can be prepared by reaction of 1-chloro-2,4-dinitrobenzene with ammonia or by acid hydrolysis of 2,4-dinitroacetanilide.
Dinitroanilines are explosive and flammable with heat or friction. Since they are made from readily obtainable raw materials, during World War I Germany used them as Ersatz high explosives.
Dinitroanilines were developed prior to 2015 by, among others, the Dow Chemical Company, who then sold their business to privately-held Gowan Company.
Dinitroanalines may have medically useful anti-microbial properties, some research has been done on trifluralin and derivatives.

## Examples

Dinitroanilines :
| Chemical name | 2,3-Dinitroaniline | 2,4-Dinitroaniline | 2,5-Dinitroaniline | 2,6-Dinitroaniline | 3,4-Dinitroaniline | 3,5-Dinitroaniline |
| Alternate name | 2,3-Dinitro-1-aminobenzene 2,3-Dinitrophenylamine 2,3-Dinitraniline | 2,4-Dinitro-1-aminobenzene 2,4-Dinitrophenylamine 2,4-Dinitraniline | 2,5-Dinitro-1-aminobenzene 2,5-Dinitrophenylamine 2,5-Dinitraniline | 2,6-Dinitro-1-aminobenzene 2,6-Dinitrophenylamine 2,6-Dinitraniline | 3,4-Dinitro-1-aminobenzene 3,4-Dinitrophenylamine 3,4-Dinitraniline | 3,5-Dinitro-1-aminobenzene 3,5-Dinitrophenylamine 3,5-Dinitraniline |
| Chemical structure | | | | | | |
| CAS Number | 602-03-9 | 97-02-9 | 619-18-1 | 606-22-4 | 610-41-3 | 618-87-1 |
| 26471-56-7 (isomeric mixture) ||||||
| PubChem | CID 136400 from PubChem | CID 7321 from PubChem | CID 123081 from PubChem | CID 69070 from PubChem | CID 136407 from PubChem | CID 12068 from PubChem |
| Chemical formula | C$_6$H$_5$N$_3$O$_4$ | C$_6$H$_5$N$_3$O$_4$ | C$_6$H$_5$N$_3$O$_4$ | C$_6$H$_5$N$_3$O$_4$ | C$_6$H$_5$N$_3$O$_4$ | C$_6$H$_5$N$_3$O$_4$ |
| Molar mass | 183.12 g/mol | 183.12 g/mol | 183.12 g/mol | 183.12 g/mol | 183.12 g/mol | 183.12 g/mol |
| Appearance | colorless to yellowish combustible powder | colorless to yellowish combustible powder | colorless to yellowish combustible powder | colorless to yellowish combustible powder | colorless to yellowish combustible powder | colorless to yellowish combustible powder |
| Melting point | | 187.8 °C | | 136 °C (decomp.) | 154–158 °C | 160–162 °C |
| Density | 1.646 g/cm (50 °C) | 1.61 g/cm | | | 1.736 g/cm | 1.601 g/cm (50 °C) |
| Solubility | soluble in water (1–2 g/L at 20 °C) | soluble in water (1–2 g/L at 20 °C) | soluble in water (1–2 g/L at 20 °C) | soluble in water (1–2 g/L at 20 °C) | soluble in water (1–2 g/L at 20 °C) | soluble in water (1–2 g/L at 20 °C) |
| GHS hazard pictograms | | | | | | |
| H- and P-phrases | | H300, H310, H330, H373, H411 | | H302, H311, H332, H373 | H301, H311, H331, H373 | H301, H311, H331, H373 |
| H- and P-phrases | | P260, P264, P273, P280, P284, P301+P310 | | P260, P301+P310, P320, P361, P405, P501 | P261, P280, P301+P310, P311 | P261, P280, P301+P310, P311 |