2-nitrotoluene

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2-nitrotoluene
2-nitrotoluene structure.png
Names
IUPAC name
1-methyl-2-nitro-benzene
Systematic IUPAC name
1-methyl-2-nitro-benzene
Other names
o-nitrotoluene
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
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.

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.

References

MSDS

Relevant Sciencemadness threads