Chemistry:Acetyl nitrate
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| Names | |
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| Preferred IUPAC name
Acetic nitric anhydride | |
| Other names
Acetyl nitrate
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| Identifiers | |
3D model (JSmol)
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| 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 | |
| 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 | |
Tracking categories (test):
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.
It is used for some nitrations and nitrolysis reactions.[2] It acetylates amines, akin to the behavior of acetyl chloride:
- [math]\ce{ 2NH3 + CH3C(O)ONO2 -> NH4NO3 + CH3CONH2 }[/math]
References
- ↑ A. Pictet, E. Khotinsky: Über Acetylnitrat. in Chem. Ber. 40, 1907, S. 1163–1166, doi:10.1002/cber.190704001172.
- ↑ Louw, Robert "Acetyl nitrate" e-EROS Encyclopedia of Reagents for Organic Synthesis 2001, 1-2. doi: 10.1002/047084289X.ra032
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