Acetyl nitrate

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.

Acetyl nitrate

Names
Preferred IUPAC name Acetic nitric anhydride
Other names Acetyl nitrate
Identifiers
CAS Number	591-09-3 Y
3D model (JSmol)	Interactive image
ChemSpider	11069
PubChem CID	11557
UNII	79CY6496CR Y
CompTox Dashboard (EPA)	DTXSID40207839
InChI InChI=1S/C2H3NO4/c1-2(4)7-3(5)6/h1H3 Key: JCZMXVGQBBATMY-UHFFFAOYSA-N
SMILES CC(=O)O[N+](=O)[O-]
Properties
Chemical formula	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). Infobox references

Synthesis and reactions

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:

(CH₃CO)₂O + HNO₃ → CH₃C(O)ONO₂ + CH₃COOH

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:

2NH₃ + CH₃C(O)ONO₂ → NH₄NO₃ + CH₃CONH₂