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Dinitromethane

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Dinitromethane
Names
Preferred IUPAC name Dinitromethane
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/CH2N2O4/c4-2(5)1-3(6)7/h1H2Key: WINNISSSXBRWMA-UHFFFAOYSA-N
  • InChI=1/CH2N2O4/c4-2(5)1-3(6)7/h1H2Key: WINNISSSXBRWMA-UHFFFAOYAE
SMILES
  • C((=O))(=O)
Properties
Chemical formula CH2N2O4
Molar mass 106.037 g·mol
Boiling point 39 to 40 °C (102 to 104 °F; 312 to 313 K) (at 2 mmHg)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Dinitromethane is an organic compound with the chemical formula CH2(NO2)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.

Synthesis

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

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

Safety

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

References

  1. ^ Legin, G. Ya.; Okhlobystina, L. V.; Fainzilberg, A. A. (1965). "Preparation of pure dinitromethane and its physical properties". Russian Chemical Bulletin. 14 (12): 2190–2191. doi:10.1007/BF00846018.
  2. Linstrom, P. J.; Mallard, W. G. (eds.). "Dinitromethane". NIST Chemistry WebBook, NIST Standard Reference Database Number 69. NIST.
  3. Villiers, R. (1884). "Sur le bromure d'èthylène tétranitré". Bulletin de la Société Chimique de France. 41: 281.
  4. Duden, P. (1893). "Ueber das Dinitromethan". Berichte der Deutschen Chemischen Gesellschaft. 26 (3): 3003–3011. doi:10.1002/cber.189302603135.
  5. Luo, K.-M., Lin, S.-H., Chang, J.-G., Huang, T.-H. (2002). "Evaluations of kinetic parameters and critical runaway conditions in the reaction system of hexamine-nitric acid to produce RDX in a non-isothermal batch reactor". Journal of Loss Prevention in the Process Industries. 15 (2): 119–127. doi:10.1016/S0950-4230(01)00027-4.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  6. "DOT Hazardous Materials". Archived from the original on 2012-04-10. Retrieved 2012-03-01.

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