Acetyl nitrate

Short description: Chemical compound

Acetyl nitrate

Names
Preferred IUPAC name

Acetic nitric anhydride

Other names

Acetyl nitrate

Identifiers

CAS Number

* 591-09-3 Y

3D model (JSmol)

* Interactive image

ChemSpider |

* 11069

PubChem CID

* 11557

UNII |

* 79CY6496CR Y

InChI

* InChI=1S/C2H3NO4/c1-2(4)7-3(5)6/h1H3

Key: JCZMXVGQBBATMY-UHFFFAOYSA-N

SMILES

* CC(=O)O[N+](=O)[O-]

Properties

Chemical formula

| 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):

* SizeSet

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

## References

1. ↑ 1.0 1.1 , 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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*[CID]: Compound ID