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	105.049 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.^[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

References

^ 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
^ Smith, Keith; Musson, Adam; Deboos, Gareth A. (1998). "A Novel Method for the Nitration of Simple Aromatic Compounds". The Journal of Organic Chemistry. 63 (23): 8448–8454. doi:10.1021/jo981557o.

[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

[3] Smith, Keith; Musson, Adam; Deboos, Gareth A. (1998). "A Novel Method for the Nitration of Simple Aromatic Compounds". The Journal of Organic Chemistry. 63 (23): 8448–8454. doi:10.1021/jo981557o.

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