2-chloropropionic acid

2-Chloropropionic acid

Names
Preferred IUPAC name 2-Chloropropanoic acid
Other names α-chloropropanoic acid α-chloropropionic acid
Identifiers
CAS Number	598-78-7 N
3D model (JSmol)	Interactive image
ChemSpider	11241 Y
ECHA InfoCard	100.009.049
InChI InChI=1S/C3H5ClO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6) Y Key: GAWAYYRQGQZKCR-UHFFFAOYSA-N Y InChI=1/C3H5ClO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6) Key: GAWAYYRQGQZKCR-UHFFFAOYAW
SMILES ClC(C(=O)O)C
Properties
Chemical formula	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
Solubility in water	Miscible
Hazards
Main hazards	Very toxic, corrosive
Safety data sheet	External MSDS
R-phrases (outdated)	R22 R26 R27 R28 R35
S-phrases (outdated)	(S1) (S2) S23 S26 S28 S36 S45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).
N  (what is YN ?)
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.

Enantiomerically pure (S)-2-chloropropionic acid is prepared from L-alanine via diazotization in hydrochloric acid. Other α-amino acids undergo this reaction.

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).

In general, α-halocarboxylic acids and their esters are good alkylating agents and should be handled with care. 2-Chloropropionic acid is a neurotoxin.