2-Nitroaniline

2-Nitroaniline
Names
	Preferred IUPAC name 2-Nitroaniline
	Systematic IUPAC name 2-Nitrobenzenamine
	Other names ortho-Nitroaniline; o-Nitroaniline
Identifiers
CAS Number	88-74-4 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL274009 ;
ChemSpider	13853943 ;
ECHA InfoCard	100.001.687
	InChI InChI=1S/C6H6N2O2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H,7H2 Key: DPJCXCZTLWNFOH-UHFFFAOYSA-N ; InChI=1/C6H6N2O2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H,7H2 Key: DPJCXCZTLWNFOH-UHFFFAOYAV;
	SMILES O=[N+]([O-])c1ccccc1N;
Properties
Chemical formula	C6H6N2O2
Molar mass	138.13 g·mol−1
Appearance	Orange solid
Density	1.442 g/mol
Melting point	71.5 °C (160.7 °F; 344.6 K)
Solubility in water	0.117 g/100 ml (20°C) (SIDS)
Magnetic susceptibility (χ)	-66.47·10−6 cm3/mol
Related compounds
Related compounds	3-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

2-Nitroaniline is an organic chemical compound that is chemically described as an aniline carrying a nitro functional group in position 2. It is also classified as an aromatic amine. At ambient temperature and pressure, 2-nitroaniline is an orange solid.^[1]

Synthesis

One method of preparing o-nitroaniline is via acetanilide. First, aniline acetylated with acetic anhydride.

C₆H₅NH₂ + (CH₃CO)₂O → C₆H₅NHC(O)CH₃ + CH₃CO₂H

In the next step, the acetanilide is nitrated:

C₆H₅NHC(O)CH₃ + HNO₃ → O₂NC₆H₄NHC(O)CH₃ + H₂O

Finally, the nitroacetanilide is hydrolyzed:

O₂NC₆H₄NHC(O)CH₃ + H₂O → O₂NC₆H₄NH₂ + CH₃CO₂H

Uses

2-Nitroaniline is the main precursor to phenylenediamines, which are converted to benzimidazoles, a family of heterocycles that are key components in pharmaceuticals.^[2]

Reactions

One of the factors contributing to the reactivity of 2-nitroaniline is the relative positioning of the nitro and amine groups and their activating/deactivating properties. The nitrogroup is an electron withdrawing group deactivating ortho and para positions. This leaves meta position with electron density and more likely to undergo substitution. Reinforcing this reactivity, the amino group activates ortho and para with respect to the amine. The net effect is that these sites, which are also meta to the nitro group undergo reactions.

References

↑ Safety data for o-nitroaniline
↑ Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411.

External links

Analysis of 2-Nitroaniline

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[1] Safety data for o-nitroaniline

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