![]() | |
Names | |
---|---|
Preferred IUPAC name Acetic nitric anhydride | |
Other names Acetyl nitrate | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
C2H3NO4 | |
Molar mass | 105.049 g·mol−1 |
Appearance | colorless liquid |
Density | 1.24 g/cm3 (15 °C) |
Boiling point | 22 °C at 70 Torr [1] |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards | explosion |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Acetyl nitrate is the organic compound with the formula CH3C(O)ONO2. It is classified as the mixed anhydride of nitric and acetic acids. It is a colorless explosive liquid that fumes in moist air.
It was first prepared in 1907 by Amé Pictet and E. Khotynsky from acetic anhydride and dinitrogen pentoxide, [1] fuming nitric acid can also be used:
It hydrolyzes in moist air to acetic acid and nitric acid. Alternatively, nitric acid adds to ketene. [2]
For aromatic nitrations, acetyl nitrate is generated in situ by mixing nitric acid with an excess of acetic anhydride in the presence of the aromatic substrate. [3]
It acetylates amines, akin to the behavior of acetyl chloride: