2-Chloropropionic acid (2-chloropropanoic acid) is the chemical compound with the formula CH<sub>3</sub>CHClCO<sub>2</sub>H. This colorless liquid is the simplest chiral chlorocarboxylic acid, and it is noteworthy for being readily available as a single enantiomer. The conjugate base of 2-chloropropionic acid (CH<sub>3</sub>CHClCO<sub>2</sub><sup>−</sup>), as well as its salts and esters, are known as 2-chloropropionates or 2-chloropropanoates.
Racemic 2-chloropropionic acid is produced by chlorination of propionyl chloride followed by hydrolysis of the 2-chloropropionyl chloride. Enantiomerically pure (S)-2-chloropropionic acid can be prepared from <small>L</small>-alanine via diazotization in hydrochloric acid. Other ñ-amino acids undergo this reaction.
Reduction of (S)-2-chloropropionic acid with lithium aluminium hydride affords (S)-2-chloropropanol, the simplest chiral chloro-alcohol. This alcohol undergoes cyclization upon treatment with potassium hydroxide, which causes dehydrohalogenation to give the epoxide, (R)-propylene oxide (methyloxirane).
2-Chloropropionyl chloride reacts with isobutylbenzene to give, after hydrolysis, ibuprofen.
In general, ñ-halocarboxylic acids and their esters are good alkylating agents and should be handled with care. 2-Chloropropionic acid is a neurotoxin.