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2-Chloropropionic acid
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<h2 id="preparation">Preparation</h2> <p>Racemic 2-chloropropionic acid is produced by chlorination of propionyl chloride followed by hydrolysis of the 2-chloropropionyl chloride.<a class="footnote-ref" id="fnref:2" href="#fn:2"><sup>2</sup></a> Enantiomerically pure (<i>S</i>)-2-chloropropionic acid can be prepared from <a href="/facts/Alanine/fphQEdSc">L-alanine</a> via <a href="/facts/Diazotization/5pkN4G5s">diazotization</a> in <a href="/facts/Hydrochloric_acid/HqItJlUT">hydrochloric acid</a>.<a class="footnote-ref" id="fnref:3" href="#fn:3"><sup>3</sup></a> Other α-<a href="/facts/Amino_acid/WDxYwBny">amino acids</a> undergo this reaction. </p> <h2 id="reactions">Reactions</h2> <p>Reduction of (<i>S</i>)-2-chloropropionic acid with <a href="/facts/Lithium_aluminium_hydride/QMMhdqEy">lithium aluminium hydride</a> affords (<i>S</i>)-2-chloropropanol, the simplest chiral chloro-alcohol. This alcohol undergoes cyclization upon treatment with <a href="/facts/Potassium_hydroxide/NBhPBuXc">potassium hydroxide</a>, which causes <a href="/facts/Dehydrohalogenation/Cx6JUTv0">dehydrohalogenation</a> to give the <a href="/facts/Epoxide/PLxRI7r1">epoxide</a>, (<i>R</i>)-<a href="/facts/Propylene_oxide/XWz8SU72">propylene oxide</a> (methyloxirane).<a class="footnote-ref" id="fnref:4" href="#fn:4"><sup>4</sup></a> </p> <p>2-Chloropropionyl chloride reacts with isobutylbenzene to give, after hydrolysis, <a href="/facts/Ibuprofen/vsKBTfVl">ibuprofen</a>.<a class="footnote-ref" id="fnref:5" href="#fn:5"><sup>5</sup></a> </p> <h2 id="safety">Safety</h2> <p>In general, α-halocarboxylic acids and their esters are good <a href="/facts/Alkylating_agent/1rd5SNbt">alkylating agents</a> and should be handled with care. 2-Chloropropionic acid is a neurotoxin.<a class="footnote-ref" id="fnref:6" href="#fn:6"><sup>6</sup></a> </p> <h2 id="see-also">See also</h2> <ul><li><a href="/facts/2%2c2-Dichloropropionic_acid/aqdBydqv">2,2-Dichloropropionic acid</a></li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>Samel, Ulf-Rainer; Kohler, Walter; Gamer, Armin Otto; Keuser, Ullrich (2005). "Propionic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_223. ISBN 978-3-527-30673-2. <a href="978-3-527-30673-2" target="_blank">978-3-527-30673-2</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>Samel, Ulf-Rainer; Kohler, Walter; Gamer, Armin Otto; Keuser, Ullrich (2005). "Propionic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_223. ISBN 978-3-527-30673-2. <a href="978-3-527-30673-2" target="_blank">978-3-527-30673-2</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>Koppenhoefer, Bernhardt; Schurig, Volker (1988). "(S)-2-Chloroalkanoic Acids of High Enantiomeric Purity from (S)-2-Amino Acids: (S)-2-Chloropropanoic Acid". Organic Syntheses. 66: 151. doi:10.15227/orgsyn.066.0151. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>Bernhard Koppenhoefer; Volker Schurig (1988). "(R)-Alkyloxiranes of High Enantiomeric Purity from (S)-2-Chloroalkanoic Acids Via (S)-2-Chloro-1-Alkanols: (R)-Methyloxirane". Organic Syntheses. 66: 160. doi:10.15227/orgsyn.066.0160. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>Samel, Ulf-Rainer; Kohler, Walter; Gamer, Armin Otto; Keuser, Ullrich (2005). "Propionic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_223. ISBN 978-3-527-30673-2. <a href="978-3-527-30673-2" target="_blank">978-3-527-30673-2</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>Simpson MG, Wyatt I, Jones HB, Gyte AJ, Widdowson PS, Lock EA (1996). "Neuropathological changes in rat brain following oral administration of 2-chloropropionic acid". Neurotoxicology. 17 (2): 471–480. PMID 8856742. <a href="/wiki/Neurotoxicology_(journal)" target="_blank">/wiki/Neurotoxicology_(journal)</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> </ol>