View source for 4-Nitroaniline

{{chembox
| verifiedrevid = 322309836
|   Name = p-Nitroaniline
|   ImageFile = p-Nitroanilin.svg
|   ImageSize = 60px
|   ImageName = p-nitroaniline|
|   OtherNames = 4-nitroaniline</br>1-amino-4-nitrobenzene</br>p-nitrophenylamine
| Section1 = {{Chembox Identifiers
|   ChemSpiderID = 7195
| CASNo_Ref = {{cascite}}
| CASNo = 100-01-6
  }}
| Section2 = {{Chembox Properties
|   Formula = C<sub>6</sub>H<sub>6</sub>N<sub>2</sub>O<sub>2</sub>
|   MolarMass = 138.12 g/mol
|   Appearance = yellow or brown powder
|   Density = 1.437 g/ml, solid
|   Solubility = 0.8 mg/ml at 18.5°C (IPCS)
|   MeltingPt = 146-149 °C(lit.)
|   BoilingPt = 332 °C
  }}
| Section7 = {{Chembox Hazards
|   ExternalMSDS = [http://www.jtbaker.com/msds/englishhtml/n4170.htm JT Baker]
|   MainHazards = Toxic
|   EUClass = {{hazchem T}} {{hazchem N}}
|   NFPA-H = 2
|   NFPA-F = 1
|   NFPA-R = 0
|   NFPA-O = 
|   RPhrases = {{R23/24/25}} {{R33}} {{R52/53}}
|   SPhrases = {{S28}} {{S36/37}} {{S45}} {{S61}}
|   FlashPt = 199 °C
  }}
| Section8 = {{Chembox Related
|   OtherCpds = [[2-Nitroaniline]], [[3-Nitroaniline]]
  }}
}}

'''4-Nitroaniline''', '''p-nitroaniline''' or '''1-amino-4-nitrobenzene''' is an organic compound with the formula C<sub>6</sub>H<sub>6</sub>N<sub>2</sub>O<sub>2</sub>.  It is an [[organic compound|organic chemical compound]], consisting of a [[benzene ring|phenyl group]] attached to an [[amino group]] which is [[Arene substitution patterns|para]] to a [[nitro group]]. The [[chemical]] structure of p-nitroaniline is shown at the right. This chemical is commonly used as an intermediate in the synthesis of dyes, antioxidants, pharmaceuticals and gasoline, in gum inhibitors, poultry medicines, and as a corrosion inhibitor.

== Synthesis ==
Below is an example synthesis of '''p-nitroaniline''' from [[aniline]]. The key step in this reaction sequence is an [[electrophilic aromatic substitution]] to install the nitro group ''para'' to the amino group. After this reaction, a separation must be performed to remove 2-nitroaniline, which is also formed in a small amount during the reaction.<ref>[http://web.centre.edu/muzyka/organic/lab/paraRed05.htm Mohrig, J.R.; Morrill, T.C.; Hammond, C.N.; Neckers, D.C. "Synthesis 5: Synthesis of the Dye Para Red from Aniline." ''Experimental Organic Chemistry.'' Freeman: New York, NY, 1997; pp 456-467].</ref><br />
[[Image:Synthesis of nitroaniline.svg|600px|]]

== Applications ==
4-Nitroaniline is a starting material for the synthesis of [[Para Red]], the first [[Azo dye]]:<ref>{{cite book
  | last = Williamson
  | first = Kenneth L.
  | title = Macroscale and Microscale Organic Experiments, Fourth Edition
  | publisher = [[Houghton-Mifflin]]
  | date = 2002
  | isbn = 0618197028}}
</ref>

[[Image:Synthesis Para Red.svg|700px|center|Synthesis of Para Red]]

== Toxicity ==
The compound is toxic by way of inhalation, ingestion, and absorption, and should be handled with care. Its [[LD50]] in rats is 750 mg/kg when administered orally. p-Nitroaniline is particularly harmful to all aquatic organisms, and can cause long-term damage to the environment if released as a pollutant.

== References ==
<references/>

== External links ==
* [http://ptcl.chem.ox.ac.uk/MSDS/NI/p-nitroaniline.html Safety (MSDS)data for p-nitroaniline]
* [http://www.jtbaker.com/msds/englishhtml/n4170.htm MSDS Sheet for ''p-''nitroaniline]
* [http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/185310 Sigma-Aldrich Catalog data]

== See also ==
* [[2-Nitroaniline]]
* [[3-Nitroaniline]]

{{DEFAULTSORT:Nitroaniline, 4-}}
[[Category:Aromatic amines]]
[[Category:Dyes]]
[[Category:Hazardous air pollutants]]
[[Category:IARC Group 3 carcinogens]]
[[Category:Nitro compounds]]

[[de:Nitroaniline]]
[[it:4-nitroanilina]]
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[[ja:4-ニトロアニリン]]
[[pt:4-Nitroanilina]]
[[Category:2Fix]]