Dinitromethane

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Dinitromethane
File:Dinitromethane.svg
File:Dinitromethane-3D-vdW.png
Names
Preferred IUPAC name
Dinitromethane
Identifiers
3D model (JSmol)
ChemSpider
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  • InChI=1S/CH2N2O4/c4-2(5)1-3(6)7/h1H2 checkY
    Key: WINNISSSXBRWMA-UHFFFAOYSA-N checkY
  • InChI=1/CH2N2O4/c4-2(5)1-3(6)7/h1H2
    Key: WINNISSSXBRWMA-UHFFFAOYAE
  • C([N+](=O)[O-])[N+](=O)[O-]
Properties
CH2N2O4
Molar mass 106.037 g·mol−1
Boiling point 39 to 40 °C (102 to 104 °F; 312 to 313 K) (at 2 mmHg)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dinitromethane is an organic compound with the chemical formula CH2(NO2)2.[2] Purified dinitromethane is a colorless liquid with a weak pleasant odor. It is relatively stable at room temperature and can be safely stored for months at 0 °C.[1]

Synthesis

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The potassium salt of dinitromethanide, KCH(NO2)2, was first prepared by Villiers in 1884 by reduction of bromodinitromethane.[3] Hydrogen fluoride and the potassium salt of dinitromethane react in diethyl ether to form dinitromethane.[1] Free dinitromethane was previously understood to be a pale, yellow oil that decomposed rapidly at ambient temperatures.[4]

Dinitromethane should not be confused with methylene dinitrate (CH2(ONO2)2), which is produced as a byproduct in the production of the explosive RDX.[5]

Safety

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The transportation of dinitromethane is forbidden by the U.S. Department of Transportation.[6]

References

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