2-Nitrotoluene

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2-nitrotoluene
200px
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 safely destroyed with Fenton's reagent.

References

MSDS

Relevant Sciencemadness threads