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,^[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

References

^ ^a ^b Amé Pictet; Eug. Khotinsky (January 1907). "Über Acetylnitrat". Berichte der Deutschen Chemischen Gesellschaft zu Berlin (in German). 40 (1): 1163–1166. doi:10.1002/CBER.190704001172. ISSN 0365-9496. Wikidata Q61714426.
^ 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.

[P-Kh-1] Amé Pictet; Eug. Khotinsky (January 1907). "Über Acetylnitrat". Berichte der Deutschen Chemischen Gesellschaft zu Berlin (in German). 40 (1): 1163–1166. doi:10.1002/CBER.190704001172. ISSN 0365-9496. Wikidata Q61714426.

[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.

[1]

[2]

[3]