2-Chloropropionic acid
# 2-Chloropropionic acid

2-Chloropropionic acid (2-chloropropanoic acid) is the chemical compound with the formula $CH_3CHClCO_2H.$ 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 $(CH_3CHClCO_2^−),$ as well as its salts and esters, are known as 2-chloropropionates or 2-chloropropanoates.

## Preparation

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 L-alanine via diazotization in hydrochloric acid. Other α-amino acids undergo this reaction.

## Reactions

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.

## Safety

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

