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Dinitroaniline

{{Short description|Class of chemical compounds}}

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.{{patent|WO|1991001292|Method for the Preparation of Nitroanilines}}

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.[https://www.dowagro.com/EN-US/NEWSROOM/PRESSRELEASES/2015/11/GOWAN-SALE dowagro.com: "Gowan Company, L.L.C. Agrees to Acquire Global DNA Business from Dow AgroSciences LLC"], 30 Nov 2015

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

Examples

class="wikitable centered" style="text-align:center; "
colspan="7" style="background: #f8eaba;" | Dinitroanilines
align="left" | Chemical name

| 2,3-Dinitroaniline

2,4-Dinitroaniline2,5-Dinitroaniline2,6-Dinitroaniline3,4-Dinitroaniline3,5-Dinitroaniline
align="left" | 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

align="left" | Chemical structure

| 80px

| 80px

| 120px

| 120px

| 80px

| 120px

rowspan="2" align="left" | CAS Number

| 602-03-9

97-02-9619-18-1606-22-4610-41-3618-87-1
colspan="6" | 26471-56-7 (isomeric mixture)
align="left" | PubChem

| {{PubChem|136400}}

{{PubChem|7321}}{{PubChem|123081}}{{PubChem|69070}}{{PubChem|136407}}{{PubChem|12068}}
align="left" | Chemical formula

| colspan="6" | C6H5N3O4

align="left" | Molar mass

| colspan="6" | 183.12 g/mol

align="left" | Appearance

| colspan="6" | colorless to yellowish combustible powder

align="left" | Melting point

|

| 187.8 °C{{GESTIS|ZVG=17550}}

|

| 136 °C (decomp.){{GESTIS|ZVG=23650}}

| 154–158 °C

| 160–162 °C{{cite web| url = http://www.sigmaaldrich.com/catalog/product/aldrich/d193402?lang=en| title = 3,5-Dinitroaniline| publisher = Sigma-Aldrich}}

class="hintergrundfarbe5" align="left" | Density

| 1.646 g/cm (50 °C){{cite book | author = C. L. Yaws | title = Thermophysical properties of chemicals and hydrocarbons | edition = 1st | page = 221 | publisher = William Andrew Inc. | location = New York | year = 2008 | isbn = 978-0-815-51596-8}}

| 1.61 g/cm

|

|

| 1.736 g/cm

| 1.601 g/cm (50 °C)

align="left" | Solubility

| colspan="6" | soluble in water (1–2 g/L at 20 °C)

align="left" | GHS hazard pictograms

|

| {{GHS01}} {{GHS06}} {{GHS08}} {{GHS09}}

|

| {{GHS01}} {{GHS06}} {{GHS08}}

| {{GHS01}} {{GHS06}} {{GHS08}}

| {{GHS01}} {{GHS06}} {{GHS08}}

align="left" rowspan="2" | H- and P-phrases

|

| {{H-phrases|300|310|330|373|411}}

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| {{H-phrases|302|311|332|373}}

| {{H-phrases|301|311|331|373}}

| {{H-phrases|301|311|331|373}}

| {{P-phrases|260|264|273|280|284|301+310}}

|

| {{P-phrases|260|301+310|320|361|405|501}}

| {{P-phrases|261|280|301+310|311}}

| {{P-phrases|261|280|301+310|311}}

References

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Category:Anilines

Category:Nitrobenzene derivatives