Ethyl propionate

Ethyl propionate
Skeletal formula of ethyl propionate
Skeletal formula of ethyl propionate
Ball-and-stick model 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
3D model (JSmol)
506287
ChemSpider
ECHA InfoCard 100.002.993 Edit this at Wikidata
EC Number
  • 203-291-4
RTECS number
  • UF3675000
UNII
UN number N119
  • InChI=1/C5H10O2/c1-3-5(6)7-4-2/h3-4H2,1-2H3
  • CCOC(=O)CC
Properties
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)
-66.5·10−6 cm3/mol
Hazards
GHS labelling:[2]
GHS02: Flammable
Danger
H225
P403+P235
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
2
0
Flash point 12 °C (54 °F; 285 K)
440 °C (824 °F; 713 K)
Explosive limits 1.9-11 %
Safety data sheet (SDS) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.

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

References

  1. ^ "Material Safety Data Sheet : Ethyl propionate" (PDF). Chemblink.com. Archived from the original (PDF) on 2014-12-05. Retrieved 2015-02-27.
  2. ^ GHS: Record of Ethyl propionate in the GESTIS Substance Database of the Institute for Occupational Safety and Health
  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.
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