Acetyl nitrate

Acetyl nitrate
Names
Other names
Nitric acetic anhydride
Identifiers
591-09-3
Properties
C2H3NO4
Molar mass 105.05
Appearance colorless liquid
Density 1.24 g/cm3 (15 °C)
Boiling point 22 °C at 10 Torr
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.[1] It acetylates amines, akin to the behavior of acetyl chloride:

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

References

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