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109274

Sigma-Aldrich

2-Chloropropionic acid

92%

Synonym(s):

(±)-2-Chloropropionic acid

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About This Item

Linear Formula:
CH3CHClCOOH
CAS Number:
598-78-7
Molecular Weight:
108.52
Beilstein:
1720259
EC Number:
209-952-3
MDL number:
MFCD00004224
UNSPSC Code:
12352100
eCl@ss:
39050312
PubChem Substance ID:
24846904
NACRES:
NA.22

vapor pressure

4 mmHg ( 20 °C)

Assay

92%

refractive index

n20/D 1.4345 (lit.)

bp

170-190 °C (lit.)

solubility

H2O: soluble

density

1.182 g/mL at 25 °C (lit.)

SMILES string

CC(Cl)C(O)=O

InChI

1S/C3H5ClO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6)

InChI key

GAWAYYRQGQZKCR-UHFFFAOYSA-N

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General description

(S)-2-Chloropropionic acid is the building block for the synthesis of aryloxyphenoxypropionic acid herbicides. 2-Chloropropionic acid is the raw material for production of pesticides, dyestuffs and agro- and forest chemicals.

Application

  • 2-Chloropropionic acid is used in the preparation of propargyl 2-chloropropionate (PCP), an atom transfer radical polymerization (ATRP) initiator, by the esterification of propargyl alcohol.
  • It can be employed in the synthesis of a biologically active chitin derivative, (1-carboxyethyl) chitosan.
  • It can be treated with o-phenylenediamine phosphate to synthesize benzimidazole derivatives.

Biochem/physiol Actions

2-Chloropropionic acid on oral administration induces necrosis of granule cell layer of rat cerebellum.

Other Notes

Contains 2,2-dichloropropionic acid

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314

Hazard Classifications

Acute Tox. 4 Oral - Skin Corr. 1A

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

215.6 °F - closed cup

Flash Point(C)

102 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of a new chitin derivative,(1-carboxyethyl) chitosan.
Shigemasa Y, et al.
Chemistry Letters (Jpn), 24(8), 623-624 (1995)
Asymmetric reduction of 2-chloroacrylic acid to (S)-2-chloropropionic acid by a novel reductase from Burkholderia sp. WS.
Kurata A, et al.
Tetrahedron Asymmetry, 15(18), 2837-2839 (2004)
A facile and ?Green? synthesis of 2-substituted benzimidazoles.
Srinivas K and Dubey P K
Der Chemica Sinica, 5(2), 114-117 (2014)
Timothy P Higgins et al.
Biodegradation, 16(5), 485-492 (2005-05-04)
We previously reported the presence of both haloalcohol and haloalkanoate dehalogenase activity in the Agrobacterium sp. strain NHG3. The versatile nature of the organism led us to further characterise the genetic basis of these dehalogenation activities. Cloning and sequencing of
R E Williams et al.
Magnetic resonance imaging, 19(2), 133-142 (2001-05-19)
L-2-Chloropropionic acid (L-CPA) is selectively toxic to rat cerebellar granule cells; necrosis is first observed about 36 hours after administration of L-CPA (750 mg/kg p.o.) becoming more marked by 48 h. Parallel to the onset of cell death an increase
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