2-Nitrotoluene
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| Names | |
|---|---|
| IUPAC name
1-methyl-2-nitro-benzene
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| Systematic IUPAC name
1-methyl-2-nitro-benzene | |
| Other names
o-nitrotoluene
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| Properties | |
| C6H4CH3NO2 | |
| Molar mass | 137.14 |
| Melting point | −10.4 °C (13.3 °F; 262.8 K) |
| Boiling point | 222 °C (432 °F; 495 K) |
| Hazards | |
| Related compounds | |
| Related compounds
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3-nitrotoluene 4-nitrotoluene |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
2-nitrotoluene, also known as o-nitrotoluene, is an isomer of mononitrotoluene. It is a yellow, oily liquid that is slightly more dense than water.
Contents
Properties
Chemical
Through many different methods, 2-nitrotoluene is oxidized to 2-nitrobenzaldehyde which is a direct precursor to indigo dye.
The nitro group on 2-nitrotoluene may be reduced to yield 2-methylaniline (2-toluidine).
Physical
2-nitrotoluene is a yellow, oily liquid. It has a strong, aromatic odor resembling almonds.
Availability
Nitrotoluenes are not available in any consumer products due to being toxic and possibly carcinogenic, and are not found in nature.
Preparation
A mixture of mononitrotoluene isomers can be prepared from the nitration of toluene between -10º and 30º C. Lower temperatures result in little or no reaction, while higher temperatures will result in double nitration forming dinitrotoluenes.
Relevant thread: Preparation of Mononitrotoluenes (o-, p-)
Projects
- Make indigo
- Make di- and trinitrotoluene
Handling
Safety
2-nitrotoluene is quite toxic and a suspected carcinogen. It must be handled with care, and should be used only in a fume hood. Care should be taken to avoid inhaling its vapors.
Storage
A glass bottle with a tight fitting, chemical resistant cap is sufficient for containing 2-nitrotoluene. For better safety, store the bottle inside of another larger container to limit exposure.
Disposal
2-Nitrotoluene can be destroyed by burning it. This must be done outside, as burning it will give off soot, carbon monoxide and other aromatic vapors.
2-nitrotoluene can be safely destroyed with Fenton's reagent. However, it's best to add very small amounts of the compound, preferably dilute, as the destruction is exothermic and may aerosolize other aromatic compounds created from the incomplete Fenton oxidation. Using a UV lamp will improve the performance of the neutralization process.
