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2-Chloropropionic acid

2-Chloropropionic acid

IUPAC name	2-Propanoic acid
Other names	α-propanoic acid; α-propanoic acid
Identifiers
CAS number	598-78-7
SMILES	CC(Cl)C(O)=O
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
Viscosity	? cP at ?°C
Hazards
MSDS	External MSDS
Main hazards	Very toxic, corrosive
R-phrases	R22 R26 R27 R28 R35
S-phrases	(S1) (S2) S23 S26 S28 S36 S45
Flash point	101 °C
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 disclaimer and 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.

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Preparation and use in organic synthesis

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 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. “S-2-Chloroalkanoic Acids of High Enantiomeric Purity from (S)-2-Amino Acids: (S)-2-Chloropropanoic Acid” Organic Syntheses, Collected Volume 8, p.119 (1993). [1]
^ Koppenhoefer, B.; Schurig, V. (R)-Alkyloxiranes of Hight Enantiomeric Purity from (S)-2-Chloroalkanoic Acids via (S)-2-Chloro-1-Alkanols: (R)-Methyloxirane” Organic Syntheses, Coll. Vol. 8, p.434 (1993). [2]
^ 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.

Categories: Carboxylic acids | Organochlorides