Ethyl propionate

Ethyl propionate is an organic compound with formula C₂H₅O₂CCH₂CH₃. It is the ethyl ester of propionic acid. It is a colorless volatile liquid with a pineapple-like odor.^[3] Some fruits such as kiwis^[4] and strawberries^[5] contain ethyl propionate in small amounts.

Ethyl propionate

Skeletal formula of ethyl propionate Ball-and-stick model of ethyl propionate
Names
Preferred IUPAC name Ethyl propanoate
Other names Ethyl propionate n-Ethyl propanoate Propanoic acid ethyl ester
Identifiers
CAS Number	105-37-3
3D model (JSmol)	Interactive image
Beilstein Reference	506287
ChemSpider	7463
ECHA InfoCard	100.002.993
EC Number	203-291-4
PubChem CID	7749
RTECS number	UF3675000
UNII	AT9K8FY49U Y
UN number	N119
CompTox Dashboard (EPA)	DTXSID1040110
InChI InChI=1/C5H10O2/c1-3-5(6)7-4-2/h3-4H2,1-2H3
SMILES CCOC(=O)CC
Properties
Chemical formula	C5H10O2
Molar mass	102.133 g·mol−1
Appearance	Colorless Liquid
Density	0.884325 g/cm3
Melting point	−73.6 °C (−100.5 °F; 199.6 K)
Boiling point	98.9 °C (210.0 °F; 372.0 K)
Magnetic susceptibility (χ)	-66.5·10−6 cm3/mol
Hazards
GHS labelling:[1]
Pictograms
Signal word	Danger
Hazard statements	H225
Precautionary statements	P403+P235
NFPA 704 (fire diamond)	2 2 0
Flash point	12 °C (54 °F; 285 K)
Autoignition temperature	440 °C (824 °F; 713 K)
Explosive limits	1.9-11 %
Safety data sheet (SDS)	[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Uses and reactions

It is also used in the production of some antimalarial drugs including pyrimethamine.^[6]

Ethyl propionate can be synthesized by the Fischer esterification of ethanol and propionic acid:

CH₃CH₂OH + CH₃CH₂CO₂H → CH₃CH₂O₂CCH₂CH₃ + H₂O

It participates in condensation reactions by virtue of the weakly acidic methylene group.^[7]

See also

• Methyl propionate, a similar compound

References

1. GHS: Record of Ethyl propionate in the GESTIS Substance Database of the Institute for Occupational Safety and Health
2. "Material Safety Data Sheet : Ethyl propionate" (PDF). Chemblink.com. Archived from the original (PDF) on 2014-12-05. Retrieved 2015-02-27.
3. "Ethyl Propionate | Cameo Chemicals | Noaa". Cameochemicals.noaa.gov. Retrieved 2015-02-27.
4. Bartley, J. P.; Schwede, A. M. (1989). "Production of volatile compounds in ripening kiwi fruit (Actinidia chinensis)". Journal of Agricultural and Food Chemistry. 37 (4): 1023. doi:10.1021/jf00088a046.
5. Perez, A. G.; Rios, J. J.; Sanz, C.; Olias, J. M. (1992). "Aroma components and free amino acids in strawberry variety Chandler during ripening". Journal of Agricultural and Food Chemistry. 40 (11): 2232. doi:10.1021/jf00023a036.
6. MacDonald, Thomas (29 January 2016). "Pyrimethamine synthesis: Status at end of 2015". Daraprim Synthesis. Open Source Malaria. Archived from the original on 26 April 2018.
7. Cox, Richard F. B.; McElvain, S. M. (1937). "Ethyl Ethoxalylpropionate". Organic Syntheses. 17: 54. doi:10.15227/orgsyn.017.0054.