Introduction
<P>Nitromethane (NM) is a colorless, oily liquid (mp -28.5 °C; bp 101.1 °C) with a
moderately strong disagreeable odor. It is a highly flammable liquid at room temperature
and reacts with alkali, strong acids, oxidizers, and metallic oxides.
[
1]
NM is completely miscible with most organic solvents. If not properly handled, stored,
or used, it can be dangerous and can detonate. The hazardous decomposition products
of NM are toxic fumes of nitrogen oxides.</P><P>Kolbe first prepared NM in 1872.
[
2]
It is synthesized by the reaction of chloroacetic acid with sodium hydroxide followed
by the treatment of sodium nitrite.
[
3]
</P><P>The versatility and synthetic ability of this reagent have been exemplified
in its increasing use in organic synthesis (e.g., pharmaceuticals, pesticides, fibers,
painting, and ore dressing).
[
4]
The potential applications of NM in the Synthesis of agricultural soil fumigants and
industrial antimicrobials have drawn much more attention. It is widely applied as
extraction solvent or reaction medium. To name a few of the many applications, NM
is used as solvent in capillary electrophoresis
[
5a]
and in the synthesis of glucosyl asparagines,
[
5b]
it also plays a role as scavenger
[
6]
of acrylonitrile in the deprotection of synthetic oligonucleotides. An enclave inclusion
compound is afforded by the recrystallization of 18-crown-6 from NM.
[
7]
With an iridium pincer complex, NM forms a coordinated ion that acts as a putative
active species in metal-catalyzed nitroaldol reactions.
[
8]
</P><P>In this Spotlight, current advances using nitromethane in organic syntheses
are emphasized with respect to stereoselectivity. The success of this reagent is related
to the unique capacity of the nitro group to be selectively converted into various
functionalities under mild conditions.</P>
