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109274

Sigma-Aldrich

2-Chloropropionic acid

92%

Synonym(s):

(±)-2-Chloropropionic acid

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100 G
$40.60
500 G
$91.10

About This Item

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

$40.60

Available to ship onApril 22, 2025Details

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vapor pressure

4 mmHg ( 20 °C)

Quality Level

100

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.)

functional group

carboxylic acid
chloro

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[1]. 2-Chloropropionic acid is the raw material for production of pesticides, dyestuffs and agro- and forest chemicals[2].

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.[3]
  • It can be employed in the synthesis of a biologically active chitin derivative, (1-carboxyethyl) chitosan.[4]
  • It can be treated with o-phenylenediamine phosphate to synthesize benzimidazole derivatives.[5]

Biochem/physiol Actions

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

Other Notes

Contains 2,2-dichloropropionic acid

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

hcodes

H302,H314

Hazard Classifications

Acute Tox. 4 Oral - Skin Corr. 1A

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 1

flash_point_f

215.6 °F - closed cup

flash_point_c

102 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
STBL3923
STBL2053
STBL0593
STBK1846
STBK0597

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A facile and ?Green? synthesis of 2-substituted benzimidazoles.
Srinivas K and Dubey P K
Der Chemica Sinica, 5(2), 114-117 (2014)
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)
Synthesis of a new chitin derivative,(1-carboxyethyl) chitosan.
Shigemasa Y, et al.
Chemistry Letters (Jpn), 24(8), 623-624 (1995)
N C Sturgess et al.
Archives of toxicology, 74(3), 153-160 (2000-07-06)
L-2-Chloropropionic acid (L-CPA), when administered orally to rats, produces selective necrosis to the granule cell layer of the rat cerebellum which is delayed in onset, not appearing until 36-48 h after exposure. The present study was conducted to characterise the
Gábor Bazsó et al.
The journal of physical chemistry. A, 116(20), 4823-4832 (2012-05-05)
Former assignments of the matrix-isolation infrared (MI-IR) spectrum of 2-chloropropionic acid are revised with the help of near-infrared (NIR) laser irradiation induced change in conformer ratios. This method allows not only the unambiguous assignment of each band in the MI-IR
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