2-Chloropropionic acid

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2-Chloropropionic acid
2-Chloropropionic acid
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number 598-78-7
ChemSpider 11241
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InChI Script error: No such module "collapsible list".
style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Molecular formula C3H4ClO2
Molar mass 108.52 g/mol
Appearance Colorless liquid
Density 1.18 g/mL
Melting point

-13 °C

Boiling point

78 °C at 10 mmHg

Solubility in water Miscible
style="background: #F8EABA; text-align: center;" colspan="2" | Hazards
MSDS External MSDS
R-phrases R22 R26 R27 R28 R35
S-phrases (S1) (S2) S23 S26 S28 S36 S45
Flash point 101 °C
style="background: #F8EABA; text-align: center;" colspan="2" | Related compounds
Related compounds Propionic acid
chloroacetic acid
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.


Enantiomerically pure S-2-chloropropionic acid is prepared from alanine via diazotization in hydrochloric acid.[1] Other α-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 with potassium hydroxide, which causes dehydrohalogenation to give the epoxide, R-methyloxirane.[2]



In general, α-halocarboxylic acids and their esters are good alkylating agents and should be handled with care. 2-Chloropropionic acid is a neurotoxin.[3]


  1. Koppenhoefer, B.; Schurig, V. (1993), "S-2-Chloroalkanoic Acids of High Enantiomeric Purity from (S)-2-Amino Acids: (S)-2-Chloropropanoic Acid", Org. Synth. ; Coll. Vol., 8: 119  Missing or empty |title= (help)
  2. Koppenhoefer, B.; Schurig, V. (1993), "(R)-Alkyloxiranes of High Enantiomeric Purity from (S)-2-Chloroalkanoic Acids via (S)-2-Chloro-1-Alkanols: (R)-Methyloxirane", Org. Synth. ; Coll. Vol., 8: 434  Missing or empty |title= (help)
  3. Simpson MG, Wyatt I, Jones HB, Gyte AJ, Widdowson PS, Lock EA. (1996). "Neuropathological changes in rat brain following oral administration of 2-chloropropionic acid". Neurotoxicology. 17 (2): 471–80. PMID 8856742. 
bs:2-hloropropionska kiselina