Dinitroaniline

Dinitroanilines are a class of chemical compounds with the chemical formula C₆H₅N₃O₄. 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.^[1]

Dinitroanilines are explosive and flammable when exposed to 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.^[2]

Dinitroanilines may have medically useful antimicrobial 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	C6H5N3O4
Molar mass	183.12 g/mol
Appearance	colorless to yellowish combustible powder
Melting point		187.8 °C[3]		136 °C (decomp.)[4]	154–158 °C	160–162 °C[5]
Density	1.646 g/cm (50 °C)[6]	1.61 g/cm[3]			1.736 g/cm	1.601 g/cm (50 °C)[6]
Solubility	soluble in water (1–2 g/L at 20 °C)
GHS hazard pictograms		[3]		[4]		[5]
H- and P-phrases		H300, H310, H330, H373, H411		H302, H311, H332, H373	H301, H311, H331, H373	H301, H311, H331, H373
		P260, P264, P273, P280, P284, P301+P310		P260, P301+P310, P320, P361, P405, P501	P261, P280, P301+P310, P311	P261, P280, P301+P310, P311