2-Chloropropionic acid
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| Names | |
|---|---|
| Preferred IUPAC name
2-Chloropropanoic acid | |
| Other names
α-chloropropanoic acid α-chloropropionic acid | |
| Identifiers | |
3D model (JSmol) |
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| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.009.049 |
| EC Number | 209-952-3 |
PubChem CID |
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| RTECS number | UE8575000 |
| UN number | 2511 |
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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 |
| GHS pictograms |     |
| GHS signal word | Danger |
| H302, H310, H314, H318, H331, H371, H373 | |
| P260, P261, P262, P264, P270, P271, P280, P301+312, P301+330+331, P302+350, P303+361+353, P304+340, P305+351+338, P309+311, P310, P311, P314, P321, P322, P330, P361, P363, P403+233, P405, P501 | |
| 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]
See also
References
- ↑ Koppenhoefer, B.; Schurig, V. (1993). "S-2-Chloroalkanoic Acids of High Enantiomeric Purity from (S)-2-Amino Acids: (S)-2-Chloropropanoic Acid". Organic Syntheses. ; Collective Volume, 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". Organic Syntheses. ; Collective Volume, 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.