2-Chloropropionic acid

2-Chloropropionic acid (2-chloropropanoic 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. The conjugate base of 2-chloropropionic acid (CH3CHClCO2−), as well as its salts and esters, are known as 2-chloropropionates or 2-chloropropanoates.[1]

2-Chloropropionic acid
2-Chloropropionic acid
Names
Preferred IUPAC name
2-Chloropropanoic acid
Other names
α-Chloropropanoic acid
α-Chloropropionic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.009.049
EC Number
  • 209-952-3
RTECS number
  • UE8575000
UNII
UN number 2511
  • InChI=1S/C3H5ClO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6) checkY
    Key: GAWAYYRQGQZKCR-UHFFFAOYSA-N checkY
  • InChI=1/C3H5ClO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6)
    Key: GAWAYYRQGQZKCR-UHFFFAOYAW
  • ClC(C(=O)O)C
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
Occupational safety and health (OHS/OSH):
Main hazards
 Toxic, corrosive
GHS labelling:
GHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Danger
H301, H302, H310, H314, H331, H371, H373
P260, P261, P262, P264, P270, P271, P280, P301+P312, P301+P330+P331, P302+P350, P303+P361+P353, P304+P340, P305+P351+P338, P309+P311, P310, P311, P314, P321, P322, P330, P361, P363, P403+P233, P405, P501
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).
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Infobox references

Preparation

Racemic 2-chloropropionic acid is produced by chlorination of propionyl chloride followed by hydrolysis of the 2-chloropropionyl chloride.[1] Enantiomerically pure (S)-2-chloropropionic acid can be prepared from L-alanine via diazotization in hydrochloric acid.[2] 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).[3]

2-Chloropropionyl chloride reacts with isobutylbenzene to give, after hydrolysis, ibuprofen.[1]

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.[4]

See also

References
  1. Samel, Ulf-Rainer; Kohler, Walter; Gamer, Armin Otto; Keuser, Ullrich (2005). "Propionic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a22_223.
  2. Koppenhoefer, Bernhardt; Schurig, Volker (1988). "(S)-2-Chloroalkanoic Acids of High Enantiomeric Purity from (S)-2-Amino Acids: (S)-2-Chloropropanoic Acid". Organic Syntheses. 66: 151. doi:10.15227/orgsyn.066.0151.
  3. Bernhard Koppenhoefer; Volker Schurig (1988). "(R)-Alkyloxiranes of High Enantiomeric Purity from (S)-2-Chloroalkanoic Acids Via (S)-2-Chloro-1-Alkanols: (R)-Methyloxirane". Organic Syntheses. 66: 160. doi:10.15227/orgsyn.066.0160.
  4. 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): 471–480. PMID 8856742.
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