Ethyl nitrate

Ethyl nitrate
Names
	IUPAC name 1-Nitrosooxyethane
	Preferred IUPAC name Ethyl nitrate
	Other names Nitric acid ethyl ester
Identifiers
CAS Number	625-58-1 ;
3D model (JSmol)	Interactive image;
ChemSpider	11756 ;
ECHA InfoCard	100.009.913
PubChem CID	12259;
UNII	E1ZT886LR5 ;
CompTox Dashboard (EPA)	DTXSID0060806 ;
	InChI InChI=1S/C2H5NO3/c1-2-6-3(4)5/h2H2,1H3 Key: IDNUEBSJWINEMI-UHFFFAOYSA-N ; InChI=1/C2H5NO3/c1-2-6-3(4)5/h2H2,1H3 Key: IDNUEBSJWINEMI-UHFFFAOYAM;
	SMILES CCO[N+](=O)[O-];
Properties
Chemical formula	C2H5NO3
Molar mass	91.066 g·mol−1
Appearance	colorless liquid
Density	1.10g/cm3
Melting point	−102 °C (−152 °F; 171 K)
Boiling point	87.5 °C (189.5 °F; 360.6 K)
Solubility in water	soluble
Hazards
NFPA 704 (fire diamond)	2 3 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
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Ethyl nitrate is the ethyl ester of nitric acid and has the chemical formula C₂H₅N O₃. It is a colourless, volatile, explosive, and extremely flammable liquid. It is used in organic synthesis and as an intermediate in the preparation of some drugs, dyes, and perfumes.[1]

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.[2]

Preparation

Ethyl nitrate has been prepared by bubbling gaseous nitryl fluoride through ethanol at −10 °C.[3] The reaction was subsequently studied in detail.[4][5]

Ethyl nitrate can be prepared by nitrating ethanol with fuming nitric acid or a mixture of concentrated sulfuric and nitric acids. Further purifying by distillation carries a risk of explosion.[6]

References

Schofield, Kenneth (1980). Aromatic nitration. Cambridge: Cambridge University Press. p. 94. ISBN 9780521233620. OCLC 6357479.
S. Perkins (August 12, 2002). "Ocean yields gases that had seemed humanmade". Science News (only available to subscribers).
G. Hetherington and R. L. Robinson (1954). "Nitryl fluoride as a nitrating agent". J. Chem. Soc.: 3512. doi:10.1039/JR9540003512.
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.
Explosives, 6th Edition, R. Meyer, J. Kohler, A. Homburg; page 125
Cohen, Julius B. (Julius Berend) (1920). Theoretical organic chemistry. University of California Libraries. London, Macmillan. p. 189.

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[1] Schofield, Kenneth (1980). Aromatic nitration. Cambridge: Cambridge University Press. p. 94. ISBN 9780521233620. OCLC 6357479.

[2] S. Perkins (August 12, 2002). "Ocean yields gases that had seemed humanmade". Science News (only available to subscribers).

[3] G. Hetherington and R. L. Robinson (1954). "Nitryl fluoride as a nitrating agent". J. Chem. Soc.: 3512. doi:10.1039/JR9540003512.

[4] 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.

[5] Explosives, 6th Edition, R. Meyer, J. Kohler, A. Homburg; page 125

[6] Cohen, Julius B. (Julius Berend) (1920). Theoretical organic chemistry. University of California Libraries. London, Macmillan. p. 189.