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Nitromethane is used as a stabilizer of halogenated organic solvents, rocket and racing fuel and a chemical intermediate. It is also used as a solvent for cyanoacrylate adhesives, polymers and waxes. It serves as a Michael donor, adding to alfa,beta-unsaturated carbonyl compounds through 1,4-addition in the Michael reaction. It acts as a solvent used for extractions, reaction medium and as a cleaning solvent. Further, it is used in the manufacture of pharmaceuticals, explosives, fibers and coatings.
For conditions for the Henry (nitro-aldol) condensation of nitroalkanes with carbonyl compounds, see 1-Nitropropane, A11975 . In the Tiffeneau-Demjanov ring expansion of ketones, the nitro aldol is reduced to the ß-hydroxyamine before diazotization; see, e.g. (cyclohexanone to cycloheptanone): Org. Synth. Coll., 4, 221 (1963); review: Org. React., 11, 157 (1960).
For a review of the use of nitro compounds as alkyl anion synthons, including methods for removing the nitro group from the resulting carbon skeletons, see: Synthesis, 833 (1988).
For reaction with TosMIC adducts to give pyrroles, see p-Toluenesulfonylmethyl isocyanide, A14312 .
For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 1174 (2007).
Brequigny, P.; Dayma, G.; Halter, F.; Mounaïm-Rousselle, C.; Dubois, T.; Dagaut, P. Laminar burning velocities of premixed nitromethane/air flames: An experimental and kinetic modeling study. Proc. Combust. Inst. 2015, 35 (1), 703-710.
Wang, C.; Wu, H. L.; Song, Y. F.; He, X.; Yang, Y. Q.; Tan, D. W. Intense pumping and time-and frequency-resolved CARS for driving and tracking structural deformation and recovery of liquid nitromethane molecules. Chem. Phys. Lett. 2015, 640, 101-105.
Gefahrenhinweise (EU): H226-H302
Flammable liquid and vapour. Harmful if swallowed.
Do not breathe dust/fume/gas/mist/vapours/spray. In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.