Ethyl nitrate

Ethyl nitrate
IUPAC name Ethyl nitrate
Other names Nitric acid ethyl ester
Identifiers
CAS number	625-58-1 Y
PubChem	12259
ChemSpider	11756 N
Jmol-3D images	{{#if:CCO[N+](=O)[O-]|Image 1
SMILES CCO[N+](=O)[O-]
InChI InChI=1S/C2H5NO3/c1-2-6-3(4)5/h2H2,1H3 N Key: IDNUEBSJWINEMI-UHFFFAOYSA-N N InChI=1/C2H5NO3/c1-2-6-3(4)5/h2H2,1H3 Key: IDNUEBSJWINEMI-UHFFFAOYAM
Properties
Molecular formula	C2H5NO3
Molar mass	91.07 g/mol
Appearance	colorless liquid
Density	1.10g/cm3
Melting point	−102 °C
Boiling point	87.5 °C
Solubility in water	Decomposes
Hazards
NFPA 704	3 2 4
Flash point	−37 °C; −34 °F; 236 K
Explosive limits	4.1%-50%
Related compounds
Related Alkyl nitrates	Methyl nitrate Ethylene glycol dinitrate Isopropyl nitrate
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Ethyl nitrate is the ethyl ester of nitric acid and has the chemical formula C₂H₅NO₃. It is a colourless, volatile, highly flammable liquid. It is used in organic synthesis and as an intermediate in the preparation of some drugs, dyes, and perfumes.^{[citation needed]}

Ethyl nitrate is found in the atmosphere, where it can react with other gases to form smog. Originally thought to be a pollutant, formed mainly by the combustion of fossil fuels, recent analysis of ocean water samples reveal that in places where cool water rises from the deep, the water is saturated with alkyl nitrates, likely formed by natural processes.^[1]

Preparation

Ethyl nitrate has been prepared by bubbling gaseous nitryl fluoride through ethanol at −10 °C.^[2] The reaction was subsequently studied in detail.^[3]

^[4]

References

1. ↑ S. Perkins (August 12, 2002). "Ocean yields gases that had seemed humanmade". Science News. 
2. ↑ G. Hetherington and R. L. Robinson (1954). "Nitryl fluoride as a nitrating agent". J. Chem. Soc.: 3512. doi:10.1039/JR9540003512. 
3. ↑ B. S. Fedorov and L. T. Eremenko (1997). "Nitration of alcohols by nitryl fluoride". Russian Chemical Bulletin 46 (5): 1022–1023. doi:10.1007/BF02496138. 
4. ↑ Explosives, 6th Edition, R. Meyer, J. Kohler, A. Homburg; page 125