Acetyl nitrate

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
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

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.

Synthesis and reactions

It was first prepared in 1907 by Amé Pictet and E. Khotynsky from acetic anhydride and dinitrogen pentoxide, 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.

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.

It acetylates amines, akin to the behavior of acetyl chloride:

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

References