2-Chloropropionic acid
 | |
| Names | |
|---|---|
| Other names
α-chloropropanoic acid; α-chloropropionic acid | |
| Identifiers | |
598-78-7  | |
| ChemSpider | 11241  |
| Jmol interactive 3D | Image |
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| 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). | |
| verify (what is ?) | |
| 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
- ↑ 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
- ↑ 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
- ↑ 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.