2-Chloropropionic acid
| 2-Chloropropionic acid | |
|---|---|
| 2-Chloropropionic acid | |
| Other names α-chloropropanoic acid; α-chloropropionic acid | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| CAS number | 598-78-7 |
| ChemSpider | 11241 |
| SMILES | Script error: No such module "collapsible list". |
| InChI | Script error: No such module "collapsible list". |
| InChI key | GAWAYYRQGQZKCR-UHFFFAOYAW |
| 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.
Contents
Preparation
Enantiomerically pure S-2-chloropropionic acid is prepared from 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 chloro-alcohol. This alcohol undergoes cyclization upon treatment with potassium hydroxide, which causes dehydrohalogenation to give the epoxide, R-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: 119 Missing or empty
|title=(help) - ↑ 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) - ↑ 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.
