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 safely destroyed with Fenton's reagent.
