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.[1]

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.[2]

It acetylates amines, akin to the behavior of acetyl chloride:

References

  1. Louw, Robert "Acetyl nitrate" e-EROS Encyclopedia of Reagents for Organic Synthesis 2001, 1-2.
  2. 10.1021/jo981557o . A Novel Method for the Nitration of Simple Aromatic Compounds . 1998 . Smith . Keith . Musson . Adam . Deboos . Gareth A. . The Journal of Organic Chemistry . 63 . 23 . 8448–8454 .

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