2-Chloropropionic acid

Chembox new
Name = 2-Chloropropionic acid
ImageFile = ClPnOH.png ImageName = 2-Chloropropionic acid
IUPACName = 2-Propanoic acid
OtherNames = α-chloropropanoic acid; α-chloropropionic acid
Section1 = Chembox Identifiers
SMILES = CC(Cl)C(O)=O
CASNo = 598-78-7
RTECS =
Section2 = Chembox Properties
Formula = C₃H₄ClO₂
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
chloroacetic acid

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 alanine via diazotization in hydrochloric acid. [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] Other α-amino acids undergo this reaction.

Reactions

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. [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]

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afety

In general, α-halocarboxylic acids and their esters are good alkylating agents and should be handled with care. 2-Chloropropionic acid is a neurotoxin. [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
year = 1996
volume = 17
issue = 2
pages = 471–80
pmid = 8856742]

References