Chemical Properties
Nitro acetate is a colorless, mobile liquid; bp 22 °C/70 mmHg,2 2-3 °C/14 mmHg;3 d 1.24 g cm-3.
Uses
Nitro acetate is used as a nitrating agent for arenes and selected nonaromatics;can functionalize alkenes to β-nitroacetates;oxidizes thioethers and disulfides to sulfoxides.
Solubility in organics
Miscible with common organic solvents.
Synthesis
The synthesis of nitro acetate: a typical approach is to add conc Nitric Acid (38 mL) slowly to stirred, cooled Acetic Anhydride (150 mL). In the earliest report,2 N2O5 was dissolved in Ac2O; though less practical, this is recommended for preparing anhydrous inorganic nitrates. Other methods involve reaction of HNO3 and ketene, or AcCl and AgNO3 in MeCN in the presence of the substrate to be nitrated.
Precautions
Nitro acetate is unstable and explosive upon heating. Isolation or distillation is not recommended unless extreme care is taken; freshly prepared solutions should be employed.Highly acidic; avoid skin contact. Reactions should be conducted in a well-ventilated fume hood.
