View source for 2-Chloropropionic acid

{{chembox
|   Name = 2-Chloropropionic acid
|   ImageFile = 2-Chloropropionic acid Enantiomers Structural Formulae.svg
|   ImageSize = 300px
|   ImageName = 2-Chloropropionic acid
|   OtherNames = &alpha;-chloropropanoic acid; &alpha;-chloropropionic acid
| Section1 = {{Chembox Identifiers
|   SMILES = ClC(C(=O)O)C
|   InChI = 1/C3H5ClO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6)
| InChIKey = GAWAYYRQGQZKCR-UHFFFAOYAW
| CASNo = 598-78-7
|   ChemSpiderID = 11241
|   RTECS = 
  }}
| Section2 = {{Chembox Properties
|   Formula = C<sub>3</sub>H<sub>4</sub>ClO<sub>2</sub>
|   MolarMass = 108.52 g/mol
|   Appearance = Colorless liquid
|   Density = 1.18 g/mL
|   Solubility = [[Miscible]]
|   MeltingPt = -13 °C
|   BoilingPt = 78 °C at 10 mmHg
|   pKa = 
|   Viscosity = 
  }}
| Section3 = {{Chembox Structure
|   Dipole =
  }}
| Section7 = {{Chembox Hazards
|   ExternalMSDS = [http://www.physchem.ox.ac.uk/MSDS/CH/2-chloropropionic_acid.html External MSDS]
|   MainHazards = Very toxic, [[corrosive]]
|   FlashPt = 101 °C
|   RPhrases = {{R22}} {{R26}} {{R27}} {{R28}} {{R35}}
|   SPhrases = {{S1}} {{S2}} {{S23}} {{S26}} {{S28}} {{S36}} {{S45}}
  }}
| Section8 = {{Chembox Related
|   OtherCpds = [[Propionic acid]]<br />[[chloroacetic acid]]
  }}
}}

'''2-Chloropropionic acid''' is the [[chemical compound]] with the formula CH<sub>3</sub>CHClCO<sub>2</sub>H. This colorless liquid is the simplest chiral chloro[[carboxylic acid]], and it is noteworthy for being readily available as a single enantiomer.

==Preparation==
Enantiomerically pure S-2-chloropropionic acid is prepared from [[alanine]] via [[diazotization]] in [[hydrochloric acid]].<ref>{{OrgSynth | author =Koppenhoefer, B.; Schurig, V. | title = S-2-Chloroalkanoic Acids of High Enantiomeric Purity from (S)-2-Amino Acids: (S)-2-Chloropropanoic Acid | collvol = 8 | collvolpages = 119 | year = 1993 | prep = cv8p0119}}</ref>  Other α-[[amino acid]]s undergo this reaction.

==Reactions==
Reduction of S-2-chloropropionic acid with [[lithium aluminium hydride]] affords S-2-chloro[[propanol]], the simplest chloro-[[alcohol]].  This alcohol undergoes cyclization upon treatment with [[potassium hydroxide]], which causes [[dehydrohalogenation]] to give the [[epoxide]], R-methyloxirane.<ref>{{OrgSynth | author = Koppenhoefer, B.; Schurig, V. | title = (R)-Alkyloxiranes of High Enantiomeric Purity from (S)-2-Chloroalkanoic Acids via (S)-2-Chloro-1-Alkanols: (R)-Methyloxirane | collvol = 8 | collvolpages = 434 | year = 1993 | prep = cv8p0434}}</ref>

:[[Image:Methyloxirane from 2-chloroproprionic acid.png|400px]]

==Safety==
In general, α-halocarboxylic acids and their esters are good [[alkylating agent]]s and should be handled with care.  2-Chloropropionic acid is a neurotoxin.<ref>{{cite journal
| title = Neuropathological changes in rat brain following oral administration of 2-chloropropionic acid.
| author = Simpson MG, Wyatt I, Jones HB, Gyte AJ, Widdowson PS, Lock EA.
| journal = [[Neurotoxicology (journal)|Neurotoxicology]]
| year = 1996
| volume = 17
| issue = 2
| pages = 471–80
| pmid = 8856742
}}</ref>

==References==
<references/>

{{DEFAULTSORT:Chloropropionic acid, 2-}}
[[Category:Carboxylic acids]]
[[Category:Organochlorides]]

[[bs:2-hloropropionska kiselina]]
[[de:2-Chlorpropionsäure]]
[[Category:2Fix]]