acetyl nitrate
{{Short description|Chemical compound, CH3C(O)ONO2}}
{{Chembox
| ImageFile = Acetyl nitrate structure.svg
| ImageSize = 160 px
| ImageAlt =
| PIN = Acetic nitric anhydride
| OtherNames = Acetyl nitrate
| Section1 = {{Chembox Identifiers
| CASNo = 591-09-3
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 79CY6496CR
| PubChem = 11557
| ChemSpiderID = 11069
| SMILES = CC(=O)O[N+](=O)[O-]
| StdInChI = 1S/C2H3NO4/c1-2(4)7-3(5)6/h1H3
| StdInChIKey = JCZMXVGQBBATMY-UHFFFAOYSA-N }}
| Section2 = {{Chembox Properties
| C=2 | H=3 | N=1 | O=4
| Appearance = colorless liquid
| Density = 1.24 g/cm3 (15 °C)
| MeltingPt =
| BoilingPt = 22 °C at 70 Torr{{Cite Q|Q61714426}}
| Solubility = }}
| Section3 = {{Chembox Hazards
| MainHazards = explosion
| FlashPt =
| AutoignitionPt = }}
}}
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.Louw, Robert "Acetyl nitrate" e-EROS Encyclopedia of Reagents for Organic Synthesis 2001, 1-2. {{doi| 10.1002/047084289X.ra032}}
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.{{cite journal |doi=10.1021/jo981557o |title=A Novel Method for the Nitration of Simple Aromatic Compounds |date=1998 |last1=Smith |first1=Keith |last2=Musson |first2=Adam |last3=Deboos |first3=Gareth A. |journal=The Journal of Organic Chemistry |volume=63 |issue=23 |pages=8448–8454 }}
It acetylates amines, akin to the behavior of acetyl chloride:
:{{chem2|2NH3 + CH3C(O)ONO2 -> NH4NO3 + CH3CONH2}}