2-Nitroaniline
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| UN number | 1661 |
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| Molar mass | Template:Chem molar mass |
| Appearance | Orange solid |
| Density | 1.442 g/ml |
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| Acidity (pKa) | −0.3 (of anilinium salt) |
| Template:Longitem | −66.47·10−6 cm3/mol |
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| Template:Longitem | 3-Nitroaniline, 4-Nitroaniline |
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2-Nitroaniline is an organic compound with the formula H2NC6H4NO2. It is a derivative of aniline, carrying a nitro functional group in position 2.[1] It is mainly used as a precursor to o-phenylenediamine.
Synthesis
2-Nitroaniline is prepared commercially by the reaction of 2-nitrochlorobenzene with ammonia:[2]
- ClC6H4NO2 + 2 NH3 → H2NC6H4NO2 + NH4Cl
Many other methods exist for the synthesis of this compound. Direct nitration of aniline is inefficient since anilinium is produced instead. Nitration of acetanilide gives only traces of 2-nitro isomer is obtained due to the great steric effect of the amide. Sulfonation is usually used to block the 4 position and increases the effectiveness to 56%.[3][4]
Uses and reactions
2-Nitroaniline is the main precursor to phenylenediamines, which are converted to benzimidazoles, a family of heterocycles that are key components in pharmaceuticals.[2]
Aside from its reduction to phenylenediamine, 2-nitroaniline undergoes other reactions anticipated for aromatic amines. It is protonated to give the anilinium salts. Owing to the influence of the nitro substituent, the amine exhibits a basicity nearly 100,000x lower than aniline itself. Diazotization gives diazonium derivative,[5] which is a precursor to some diazo dyes. Acetylation affords 2-nitroacetanilide.
See also
References
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External links
- Analysis of 2-Nitroaniline Script error: No such module "webarchive".