Acetyl nitrate explained

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 + CH₃COOHIt 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.^[1] It acetylates amines, akin to the behavior of acetyl chloride:

2NH3 + CH3C(O)ONO2 -> NH4NO3 + CH3CONH2

References

1. Louw, Robert "Acetyl nitrate" e-EROS Encyclopedia of Reagents for Organic Synthesis 2001, 1-2.

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