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).
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Infobox references

3-Nitroaniline is an organic compound with the formula H2NC6H4NO2. A yellow solid, it is a derivative of aniline, carrying a nitro functional group in position 3. It is an isomer of 2-nitroaniline and 4-nitroaniline. It is used as a precursor to dyes.[1]

Synthesis and applications

Structure of disperse yellow 5, a disperse dye derived from 3-nitroaniline.

3-Nitroaniline is produced on a commercial scale by reduction of 1,3-dinitrobenzene with hydrogen sulfide:[1]

In principle it can also be prepared by nitration of benzamide followed by the Hofmann rearrangement of the resulting 3-nitrobenzamide. The reaction involves treating the 3-nitrobenzamide with sodium hypobromite or sodium hypochlorite to transform the amide group into an amine.

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.

References

  1. 1 2 Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 978-3527306732.
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