Acetyl nitrate

Acetyl nitrate
Names
	Preferred IUPAC name Acetic nitric anhydride
	Other names Acetyl nitrate
Identifiers
CAS Number	591-09-3 ;
3D model (JSmol)	Interactive image;
ChemSpider	11069;
PubChem CID	11557;
UNII	79CY6496CR ;
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	105.05
Appearance	colorless liquid
Density	1.24 g/cm3 (15 °C)
Boiling point	22 °C at 70 Torr [1]
Hazards
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 is prepared from acetic anhydride and dinitrogen pentoxide or with nitric acid:

(CH₃CO)₂O + HNO₃ → CH₃C(O)ONO₂ + CH₃CO₂H

It hydrolyzes in air to acetic and nitric acid, the reverse of the above reaction. Alternatively, nitric acid adds to ketene.

It is used for some nitrations and nitrolysis reactions.[2] It acetylates amines, akin to the behavior of acetyl chloride:

2 RNH₂ + CH₃C(O)ONO₂ → [RNH₃]NO₃ + CH₃C(O)NHR

References

[1]

A. Pictet, E. Khotinsky: Über Acetylnitrat. in Chem. Ber. 40, 1907, S. 1163–1166, doi:10.1002/cber.190704001172.
Louw, Robert "Acetyl nitrate" e-EROS Encyclopedia of Reagents for Organic Synthesis 2001, 1-2. doi: 10.1002/047084289X.ra032

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[Pictet-1] A. Pictet, E. Khotinsky: Über Acetylnitrat. in Chem. Ber. 40, 1907, S. 1163–1166, doi:10.1002/cber.190704001172.

[2] Louw, Robert "Acetyl nitrate" e-EROS Encyclopedia of Reagents for Organic Synthesis 2001, 1-2. doi: 10.1002/047084289X.ra032