Density 1.18 g/cm³ | Appearance Colorless liquid | |
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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.
Contents
Preparation
Enantiomerically pure (S)-2-chloropropionic acid is 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).
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.