:Ethyl propionate

{{Chembox

| Name =

| ImageFileL1 = Ethyl-propionate-2D-skeletal.svg

| ImageNameL1 = Skeletal formula of ethyl propionate

| ImageSizeL1 = 120px

| ImageFileR1 = Ethyl propionate 3D ball.png

| ImageNameR1 = Ball-and-stick model of ethyl propionate

| ImageSizeR1 = 120px

| ImageFile2 = Ethyl propionate.jpg

| ImageSize2 = 50px

| ImageAlt = Skeletal formula of ethyl propionate

| PIN = Ethyl propanoate

| OtherNames = {{bulleted list|Ethyl propionate |n-Ethyl propanoate|Propanoic acid ethyl ester}}

|Section1={{Chembox Identifiers

| Abbreviations =

| CASNo = 105-37-3

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = AT9K8FY49U

| PubChem = 7749

| ChemSpiderID = 7463

| EINECS = 203-291-4

| UNNumber = N119

| RTECS = UF3675000

| SMILES = CCOC(=O)CC

| InChI = 1/C5H10O2/c1-3-5(6)7-4-2/h3-4H2,1-2H3

| Beilstein = 506287}}

|Section2={{Chembox Properties

| C=5|H=10|O=2

| Density = 0.884325 g/cm3

| MeltingPtC = -73.6

| BoilingPtC = 98.9

| Appearance = Colorless Liquid

| MagSus = −66.5·10−6 cm3/mol

}}

|Section7={{Chembox Hazards

| ExternalSDS = {{cite web |url=http://www.chemblink.com/MSDS/MSDSFiles/105-37-3_Sigma-Aldrich.pdf |title=Material Safety Data Sheet : Ethyl propionate |publisher=Chemblink.com |access-date=2015-02-27 |archive-date=2014-12-05 |archive-url=https://web.archive.org/web/20141205065737/http://www.chemblink.com/MSDS/MSDSFiles/105-37-3_Sigma-Aldrich.pdf |url-status=dead }}

| GHSPictograms = {{GHS02}}

| GHSSignalWord = danger

| HPhrases = {{HPhrases|H225}}

| PPhrases = {{PPhrases|P403+P235}}

| GHS_ref = GHS: {{GESTIS|ZVG=28580|CAS=105-37-3|Name=Ethyl propionate}}

| NFPA-H = 2

| NFPA-F = 2

| NFPA-R = 0

| FlashPtC = 12

| AutoignitionPtC = 440

| ExploLimits = 1.9-11 %

}}

}}

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.{{cite web|url=http://cameochemicals.noaa.gov/chemical/710 |title=Ethyl Propionate | Cameo Chemicals | Noaa |publisher=Cameochemicals.noaa.gov |access-date=2015-02-27}} Some fruits such as kiwis{{Cite journal | last1 = Bartley | first1 = J. P. | last2 = Schwede | first2 = A. M. | doi = 10.1021/jf00088a046 | title = Production of volatile compounds in ripening kiwi fruit (Actinidia chinensis) | journal = Journal of Agricultural and Food Chemistry | volume = 37 | issue = 4 | pages = 1023 | year = 1989 }} and strawberries{{Cite journal | last1 = Perez | first1 = A. G. | last2 = Rios | first2 = J. J. | last3 = Sanz | first3 = C. | last4 = Olias | first4 = J. M. | title = Aroma components and free amino acids in strawberry variety Chandler during ripening | doi = 10.1021/jf00023a036 | journal = Journal of Agricultural and Food Chemistry | volume = 40 | issue = 11 | pages = 2232 | year = 1992 }} contain ethyl propionate in small amounts.

Uses and reactions

It is also used in the production of some antimalarial drugs including pyrimethamine.{{cite web|title=Pyrimethamine synthesis: Status at end of 2015|website=Daraprim Synthesis|publisher=Open Source Malaria|date=29 January 2016|first=Thomas|last=MacDonald|archive-url=https://web.archive.org/web/20180426233859/http://malaria.ourexperiment.org/daraprim_synthesis/13962/Pyrimethamine_synthesis_Status_at_end_of_2015.html|archive-date=26 April 2018|url=http://malaria.ourexperiment.org/daraprim_synthesis/13962/Pyrimethamine_synthesis_Status_at_end_of_2015.html}}

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.{{cite journal|first1=Richard F. B.|last1=Cox|first2=S. M.|last2=McElvain |doi=10.15227/orgsyn.017.0054|title=Ethyl Ethoxalylpropionate|journal=Organic Syntheses|year=1937|volume=17|page=54}}

See also

References