2-Chloropropionic acid

2-Chloropropionic acid
Names
Other names
α-chloropropanoic acid; α-chloropropionic acid
Identifiers
598-78-7 N
ChemSpider 11241 YesY
Jmol interactive 3D Image
Properties
C3H5ClO2
Molar mass 108.52 g·mol−1
Appearance Colorless liquid
Density 1.18 g/mL
Melting point −13 °C (9 °F; 260 K)
Boiling point 78 °C (172 °F; 351 K) at 10 mmHg
Miscible
Hazards
Main hazards Very toxic, corrosive
Safety data sheet External MSDS
R-phrases R22 R26 R27 R28 R35
S-phrases (S1) (S2) S23 S26 S28 S36 S45
Flash point 101 °C (214 °F; 374 K)
Related compounds
Related compounds
Propionic acid
Chloroacetic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.

Preparation

Enantiomerically pure (S)-2-chloropropionic acid is prepared from L-alanine via diazotization in hydrochloric acid.[1] 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]

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.[3]

References

  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, p. 119
  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, p. 434
  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.
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