2-Chloropropionic acid

2-Chloropropionic acid
Names
	Other names α-chloropropanoic acid; α-chloropropionic acid
Identifiers
CAS Number	598-78-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	11241 ;
ECHA InfoCard	100.009.049
CompTox Dashboard (EPA)	DTXSID0021545 ;
	InChI InChI=1S/C3H5ClO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6) Key: GAWAYYRQGQZKCR-UHFFFAOYSA-N ; 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
	Occupational safety and health (OHS/OSH):
Main hazards	Very toxic, corrosive
Flash point	101 °C (214 °F; 374 K)
Safety data sheet (SDS)	External MSDS
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". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, 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". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[1] Koppenhoefer, B.; Schurig, V. (1993). "S-2-Chloroalkanoic Acids of High Enantiomeric Purity from (S)-2-Amino Acids: (S)-2-Chloropropanoic Acid". Organic Syntheses{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 8, p. 119.

[2] 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{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 8, p. 434.

[3] 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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