2-Chloropropionic acid
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Template:Chembox image cellTemplate:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox SolubilityInWaterTemplate:Chembox headerbarTemplate:Chembox OHS (set)Template:Chembox GHS (set)Template:Chembox SDSTemplate:Chembox headerbarTemplate:Chembox Datapage checkTemplate:Chembox Footer| Template:Longitem | Template:Unbulleted list |
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| UN number | 2511 |
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| Appearance | Colorless liquid |
| Density | 1.18 g/mL |
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| Template:Longitem | Propionic acid Chloroacetic acid |
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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.[1]
Preparation
Racemic 2-chloropropionic acid is produced by chlorination of propionyl chloride followed by hydrolysis of the 2-chloropropionyl chloride.[1] Enantiomerically pure (S)-2-chloropropionic acid can be prepared from L-alanine via diazotization in hydrochloric acid.[2] 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).[3]
2-Chloropropionyl chloride reacts with isobutylbenzene to give, after hydrolysis, ibuprofen.[1]
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.[4]
See also
References
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