Chemistry:Acetyl nitrate
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Short description: Chemical compound
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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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| ChemSpider | |
PubChem CID
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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,[1] 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.[2]
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.[3]
It acetylates amines, akin to the behavior of acetyl chloride:
- 2NH
3 + CH
3C(O)ONO
2 → NH
4NO
3 + CH
3CONH
2
References
- ↑ 1.0 1.1 , Wikidata Q61714426
- ↑ Louw, Robert "Acetyl nitrate" e-EROS Encyclopedia of Reagents for Organic Synthesis 2001, 1-2. doi: 10.1002/047084289X.ra032
- ↑ 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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