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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.

Dinitroanilines are intermediates in the preparation of various industrially important chemicals including dyes and pesticides. Herbicides which are derivatives of dinitroanilines, and 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 and pendimethalin are the most widely commercially used.

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 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.[2]

Dinitroanalines may have medically useful anti-microbial properties, some research has been done on trifluralin and derivatives.

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
 GHS01: Explosive GHS06: Toxic GHS08: Health hazard GHS09: Environmental hazard[3] GHS01: Explosive GHS06: Toxic GHS08: Health hazard[4] GHS01: Explosive GHS06: Toxic GHS08: Health hazard GHS01: Explosive GHS06: Toxic GHS08: Health hazard[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

References

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  1. ^ WO 1991001292  Method for the Preparation of Nitroanilines
  2. ^ dowagro.com: "Gowan Company, L.L.C. Agrees to Acquire Global DNA Business from Dow AgroSciences LLC", 30 Nov 2015
  3. ^ a b c Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  4. ^ a b Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  5. ^ a b "3,5-Dinitroaniline". Sigma-Aldrich.
  6. ^ a b C. L. Yaws (2008). Thermophysical properties of chemicals and hydrocarbons (1st ed.). New York: William Andrew Inc. p. 221. ISBN 978-0-815-51596-8.