2-Chloropropionic acid

2-Chloropropionic acid is the chemical compound with the formula CH3CHClCO2H. This colorless liquid is the simplest chiral chlorocarboxylic acid, and it is noteworthy for being readily available as a single enantiomer.

Preparation and use in organic synthesis
Enantiomerically pure S-2-chloropropionic acid is prepared from alanine via diazotization in hydrochloric acid. Other &alpha;-amino acids undergo this reaction.

Reduction of S-2-chloropropionic acid with lithium aluminium hydride affords S-2-chloropropanol, the simplest chloro-alcohol. This alcohol undergoes cyclization upon treatment potassium hydroxide, which causes dehydrohalogenation to give the epoxide, R-methyloxirane.

Safety
In general, &alpha;-halocarboxylic acids and their esters are good alkylating agents and should be handled with care. 2-Chloropropionic acid is a neurotoxin.