2,4-Dinitrobromobenzene

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2,4-Dinitrobromobenzene
2,4-dinitrobromobenzene.png
Structure of the compound
Names
IUPAC name
1-Bromo-2,4-dinitrobenzene
Other names
O,p-Dinitrophenyl bromide
Properties
C6H3BrN2O4
Molar mass 247.004 g/mol
Density 1.91 g/cm3
Melting point 70–73 °C (158–163 °F; 343–346 K)
Slightly soluble
Solubility Soluble in diethyl ether, ethanol, methanol
Hazards
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

2,4-Dinitrobromobenzene is a useful organic intermediate and is readily prepared in a laboratory.

Properties

Chemical

2,4-Dinitrobromobenzene is soluble in water and methanol. It is reactive towards reducing agents such as Sn/HCl and H2/Pd to form 2,4-diaminobromobenzene.

Physical

2,4-Dinitrobromobenzene, when pure, is a light yellow crystalline substance which melts at 71°C-73°C. It has the characteristic slightly sweet smell of nitroaromatic compounds, though it is toxic and inhalation of the dust should be avoided. It has a density of 1.91 g/cm3.

Availability

2,4-Dinitrobromobenzene is not offered by any suppliers available to the amateur. However, 2,4 dinitrochlorobenzene may be available from chemical suppliers and finds similar uses.

Preparation

2,4-Dinitrobromobenzene can be prepared with relative ease in a home lab by the nitration of bromobenzene. A writeup of this reaction is available here.

Projects

Handling

Safety

2,4-Dinitrobromobenzene is a mutagen and skin irritant. Skin contact should be avoided by wearing gloves as some people possess a severe allergy to the compound, resulting in contact dermatitis of varying severity. It may have shock sensitivity, though the extent of which is currently undocumented.

Storage

In closed glass bottles, away from any flame source or light.

Disposal

It can be destroyed with Fenton's reagent. The best way is to dissolve it in a solvent and add it dropwise to the Fenton solution, to limit splashing and aerosolization of the compound.

References

Relevant Sciencemadness threads