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Acetyl nitrate

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Acetyl nitrate
Names
Preferred IUPAC name Acetic nitric anhydride
Other names Acetyl nitrate
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H3NO4/c1-2(4)7-3(5)6/h1H3Key: JCZMXVGQBBATMY-UHFFFAOYSA-N
SMILES
  • CC(=O)O(=O)
Properties
Chemical formula C2H3NO4
Molar mass 105.049 g·mol
Appearance colorless liquid
Density 1.24 g/cm (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 , 100 kPa). Infobox references
Chemical compound

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 + CH3COOH

It hydrolyzes in moist air to acetic acid and nitric acid. Alternatively, nitric acid adds to ketene.

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.

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

2NH3 + CH3C(O)ONO2 → NH4NO3 + CH3CONH2

References

  1. ^ Amé Pictet; Eug. Khotinsky (January 1907). "Über Acetylnitrat". Berichte der Deutschen Chemischen Gesellschaft (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.
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