3-Nitroaniline

3-Nitroaniline, also known as meta-nitroaniline and m-nitroaniline, is a non-volatile stable solid commonly used as a raw material for dyes.[1] 3-Nitroaniline is an aniline carrying a nitro functional group in position 3. It is stable in neutral, acidic or alkaline solutions and is classified as "not readily biodegradable" with "low bioaccumulation potential".[1]

3-Nitroaniline
Skeletal formula of 3-nitroaniline
Ball-and-stick model of the 3-nitroaniline molecule
Names
Preferred IUPAC name
3-Nitroaniline
Systematic IUPAC name
3-Nitrobenzenamine
Other names
meta-Nitroaniline
m-Nitroaniline
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.002.481
EC Number
  • 202-729-1
RTECS number
  • BY6825000
UNII
UN number 1661
  • InChI=1S/C6H6N2O2/c7-5-2-1-3-6(4-5)8(9)10/h1-4H,7H2 checkY
    Key: XJCVRTZCHMZPBD-UHFFFAOYSA-N checkY
  • InChI=1/C6H6N2O2/c7-5-2-1-3-6(4-5)8(9)10/h1-4H,7H2
    Key: XJCVRTZCHMZPBD-UHFFFAOYAY
  • O=[N+]([O-])c1cccc(N)c1
Properties
C6H6N2O2
Molar mass 138.126 g·mol−1
Appearance Yellow solid
Density 0.9011
Melting point 114 °C (237 °F; 387 K)
Boiling point 306 °C (583 °F; 579 K)
0.1 g/100 ml (20 °C)
Acidity (pKa) 2.47
-70.09·10−6 cm3/mol
Hazards
GHS labelling:
GHS06: ToxicGHS08: Health hazard
Danger
H301, H311, H331, H373, H412
P260, P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P311, P312, P314, P321, P322, P330, P361, P363, P403+P233, P405, P501
Related compounds
Related compounds
 2-Nitroaniline, 4-Nitroaniline
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

It is used as a chemical intermediate for azo coupling component 17 and the dyes disperse yellow 5 and acid blue 29. The chemical is changed to other substances (dyestuffs and m-nitrophenol) during the dyeing process.

Synthesis

It can be synthesized by nitration of benzamide followed by the Hofmann rearrangement of the 3-nitrobenzamide previously formed. It consist in treating the 3-nitrobenzamide with sodium hypobromite or sodium hypochlorite to transform the amide group into an amine.

See also

References
  1. "UNEP PDF on m-Nitroaniline" (PDF). Archived from the original (PDF) on 2016-03-06. Retrieved 2006-10-10.
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