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Acetyl nitrate

From Wikipedia, the free encyclopedia
Acetyl nitrate
Names
Preferred IUPAC name
Acetic nitric anhydride
Other names
Acetyl nitrate
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C2H3NO4/c1-2(4)7-3(5)6/h1H3
    Key: JCZMXVGQBBATMY-UHFFFAOYSA-N
  • CC(=O)O[N+](=O)[O-]
Properties
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).

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

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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.

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

References

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  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

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