Surf Wiki
Save to docs
general/carboxylic-acids

From Surf Wiki (app.surf) — the open knowledge base

2-Chloropropionic acid

α-Chloropropionic acid Chloroacetic acid

2-Chloropropionic acid (2-chloropropanoic 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. The conjugate base of 2-chloropropionic acid (CH3CHClCO2−), 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. 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).

:[[Image:Methyloxirane from 2-chloropropionic acid.png|400px]]

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.

References

References

  1. (2005). "Propionic Acid and Derivatives".
  2. (1988). "(S)-2-Chloroalkanoic Acids of High Enantiomeric Purity from (S)-2-Amino Acids: (S)-2-Chloropropanoic Acid". Organic Syntheses.
  3. (1988). "(R)-Alkyloxiranes of High Enantiomeric Purity from (S)-2-Chloroalkanoic Acids Via (S)-2-Chloro-1-Alkanols: (R)-Methyloxirane". Organic Syntheses.
  4. (1996). "Neuropathological changes in rat brain following oral administration of 2-chloropropionic acid". [[Neurotoxicology (journal).
Info: Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

carboxylic-acids organochlorides
Want to explore this topic further?

Ask Mako anything about 2-Chloropropionic acid — get instant answers, deeper analysis, and related topics.

Research with Mako

Free with your Surf account

Content sourced from Wikipedia, available under CC BY-SA 4.0.

This content may have been generated or modified by AI. CloudSurf Software LLC is not responsible for the accuracy, completeness, or reliability of AI-generated content. Always verify important information from primary sources.

Report