At least some naturally occurring nitro groups arose by the oxidation of amino groups. Occurrence In nature Ĭhloramphenicol is a rare example of a naturally occurring nitro compound. When the same reactant is reacted with potassium hydroxide the reaction product is the 1,2-dinitro dimer. The reaction mechanism is proposed in which in the first slow step a proton is abstracted from nitroalkane 1 to a carbanion 2 followed by protonation to an aci-nitro 3 and finally nucleophilic displacement of chlorine based on an experimentally observed hydrogen kinetic isotope effect of 3.3. In the so-called Ter Meer reaction (1876) named after Edmund ter Meer, the reactant is a 1,1-halonitroalkane: In nucleophilic aliphatic substitution, sodium nitrite (NaNO 2) replaces an alkyl halide. By decarboxylation of α-nitro carboxylic acids formed from nitriles and ethyl nitrate.Reduction of β-nitro alcohols or nitroalkenes.Oxidation of oximes or primary amines.Nitromethane can be produced in the laboratory by treating sodium chloroacetate with sodium nitrite.Nucleophilic substitution reactions between halocarbons or organosulfates with silver or alkali nitrite salts.The reaction produces fragments from the parent alkane, creating a diverse mixture of products for instance, nitromethane, nitroethane, 1-nitropropane, and 2-nitropropane are produced by treating propane with nitric acid in the gas phase (e.g. Preparation of aliphatic nitro compounds Īliphatic nitro compounds can be synthesized by various methods notable examples include:

Īnother but more specialized method for making aryl–NO 2 group starts from halogenated phenols, is the Zinke nitration. Many explosives are produced by nitration including trinitrophenol (picric acid), trinitrotoluene (TNT), and trinitroresorcinol (styphnic acid).

The nitration product produced on the largest scale, by far, is nitrobenzene.

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