3385-94-2

clear colorless to slightly yellow liquid

bp 164°C; d 0.846 g cm?3.

Bis(trimethylsilyl) sulfide (TMS2S) is used to reduce aromatic nitro groups to amines and the oxides of sulfur, selenium, and tellurium. Conditions for nitro group reduction (eq 1) are forcing; however, yields are good. Reactions of TMS2S with primary aliphatic nitro groups result in the formation of the thiohydroxamic acids (eq 2) which can be isolated or carried further to the nitrile. Secondary alkyl nitro derivatives provide oximes. Sulfoxides are reduced to sulfides, selenoxides to selenides, and telluroxides to tellurides. Conditions are mild and work well on both the aliphatic and aromatic oxides.

Dissolve it in pet ether (b ca 40o), remove the solvent and distil it. Redistil it under atmospheric pressure of dry N2. It is collected as a colourless liquid which solidifies to a white solid in Dry-ice. On standing for several days it turns yellow possibly due to liberation of sulfur. Store it below 4o under dry N2. [Eaborn J Chem Soc 3077 1950, Beilstein 4 IV 4033.]