View source for Chemistry:Dinitroaniline

{{Short description|Class of chemical compounds}}
'''Dinitroanilines''' are a class of [[Chemistry:Chemical compound|chemical compound]]s with the chemical formula C<sub>6</sub>H<sub>5</sub>N<sub>3</sub>O<sub>4</sub>.  They are derived from both [[Chemistry:Aniline|aniline]] and [[Chemistry:Dinitrobenzene|dinitrobenzene]]s.  There are six [[Chemistry:Isomer|isomer]]s: 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 [[Engineering:Chemical industry|industrially]] important chemicals including dyes and [[Biology:Pesticide|pesticide]]s.  [[Biology:Herbicide|Herbicide]]s which are [[Chemistry:Derivative|derivatives]] of dinitroanilines include [[Chemistry:Benfluralin|benfluralin]], butralin, chlornidine, dinitramine, dipropalin, ethalfluralin, fluchloralin, isopropalin, methalpropalin, nitralin, [[Chemistry:Oryzalin|oryzalin]], [[Chemistry:Pendimethalin|pendimethalin]], [[Chemistry:Prodiamine|prodiamine]], profluralin, and [[Chemistry:Trifluralin|trifluralin]].

2,4-Dinitroaniline can be prepared by reaction of 1-chloro-2,4-dinitrobenzene with ammonia or by acid hydrolysis of 2,4-dinitroacetanilide.<ref>{{patent|WO|1991001292|Method for the Preparation of Nitroanilines}}</ref>

Dinitroanilines are explosive and flammable with heat or friction.

Dinitroanilines were developed prior to 2015 by, among others, the [[Company:Dow Chemical Company|Dow Chemical Company]], who then sold their business to privately-held Gowan Company.<ref>[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</ref>

{| class="wikitable centered" style="text-align:center; "
|-
| colspan="7" style="background: #f8eaba;" | '''Dinitroanilines'''
|-
| align="left" | Chemical name
| 2,3-Dinitroaniline || 2,4-Dinitroaniline || 2,5-Dinitroaniline || 2,6-Dinitroaniline || 3,4-Dinitroaniline || 3,5-Dinitroaniline
|-
| align="left" | Alternate name
| 2,3-Dinitro-1-aminobenzene<br>2,3-Dinitrophenylamine<br>2,3-Dinitraniline
| 2,4-Dinitro-1-aminobenzene <br>2,4-Dinitrophenylamine<br>2,4-Dinitraniline
| 2,5-Dinitro-1-aminobenzene <br>2,5-Dinitrophenylamine<br>2,5-Dinitraniline
| 2,6-Dinitro-1-aminobenzene <br>2,6-Dinitrophenylamine<br>2,6-Dinitraniline
| 3,4-Dinitro-1-aminobenzene <br>3,4-Dinitrophenylamine<br>3,4-Dinitraniline
| 3,5-Dinitro-1-aminobenzene <br>3,5-Dinitrophenylamine<br>3,5-Dinitraniline
|-
| align="left" | [[Chemistry:Chemical structure|Chemical structure]]
| [[File:2,3-Dinitroanilin.svg|80px]]
| [[File:2,4-Dinitroanilin.svg|80px]]
| [[File:2,5-Dinitroanilin.svg|120px]]
| [[File:2,6-Dinitroanilin.svg|120px]]
| [[File:3,4-Dinitroanilin.svg|80px]]
| [[File:3,5-Dinitroanilin.svg|120px]]
|-
| rowspan="2" align="left" | CAS Number
| 602-03-9 || 97-02-9 || 619-18-1 || 606-22-4 || 610-41-3 || 618-87-1
|-
| colspan="6" | 26471-56-7 (isomeric mixture)
|-
| align="left" | [[Biology:PubChem|PubChem]]
| {{PubChem|136400}} || {{PubChem|7321}} || {{PubChem|123081}} || {{PubChem|69070}} || {{PubChem|136407}} || {{PubChem|12068}}
|-
| align="left" | [[Chemistry:Chemical formula|Chemical formula]]
| colspan="6" | C<sub>6</sub>H<sub>5</sub>N<sub>3</sub>O<sub>4</sub>
|-
| align="left" | [[Physics:Molar mass|Molar mass]]
| colspan="6" | 183.12 g/mol
|-
| align="left" | Appearance
| colspan="6" | colorless to yellowish combustible powder
|-
| align="left" | [[Physics:Melting point|Melting point]]
|
| 187.8&nbsp;°C<ref name="GESTIS_2">{{GESTIS|ZVG=17550}}</ref>
|
| 136 °C (decomp.)<ref name="GESTIS_4">{{GESTIS|ZVG=23650}}</ref>
| 154–158&nbsp;°C
| 160–162&nbsp;°C<ref name=sigmaaldrich>{{cite web| url = http://www.sigmaaldrich.com/catalog/product/aldrich/d193402?lang=en| title = 3,5-Dinitroaniline| publisher = [[Company:Sigma-Aldrich|Sigma-Aldrich]]}}</ref>
|-
| class="hintergrundfarbe5" align="left" | [[Physics:Density|Density]]
| 1.646 g/cm (50&nbsp;°C)<ref name="Yaws">{{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}}</ref>
| 1.61 g/cm<ref name="GESTIS_2" />
|
|
| 1.736 g/cm
| 1.601 g/cm (50&nbsp;°C)<ref name="Yaws"/>
|-
| align="left" | [[Chemistry:Solubility|Solubility]]
| colspan="6" | soluble in water (1–2 g/L at 20 °C)
|-
|  align="left" | [[GHS hazard pictograms]]<br/>
| 
| {{GHS01}} {{GHS06}} {{GHS08}} {{GHS09}}<ref name="GESTIS_2" />
| 
| {{GHS01}} {{GHS06}} {{GHS08}}<ref name="GESTIS_4" />
| {{GHS01}} {{GHS06}} {{GHS08}}
| {{GHS01}} {{GHS06}} {{GHS08}}<ref name=sigmaaldrich/>
|-
| align="left" rowspan="2" | H- and P-phrases
| 
| {{H-phrases|300|310|330|373|411}}
| 
| {{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==
{{reflist}}

[[Category:Anilines]]
[[Category:Nitrobenzene derivatives]]

{{Sourceattribution|Dinitroaniline}}