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Merck
CN

109274

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
NACRES:
NA.22
PubChem Substance ID:
24846904
eCl@ss:
39050312
UNSPSC Code:
12352100
EC Number:
209-952-3
MDL number:
MFCD00004224
Beilstein/REAXYS Number:
1720259

Key Documents

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Product Name

2-Chloropropionic acid, 92%

InChI key

GAWAYYRQGQZKCR-UHFFFAOYSA-N

InChI

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

SMILES string

CC(Cl)C(O)=O

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.)

functional group

carboxylic acid
chloro

Quality Level

100

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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.

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.

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

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB4754
STBL3923
STBL2053
STBL0593
STBK1846

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Synthesis of well-defined cyclic poly (N-isopropylacrylamide) via click chemistry and its unique thermal phase transition behavior.
Xu J, et al.
Macromolecules, 40(25), 9103-9110 (2007)
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)
A facile and ?Green? synthesis of 2-substituted benzimidazoles.
Srinivas K and Dubey P K
Der Chemica Sinica, 5(2), 114-117 (2014)
B B Aam et al.
Toxicology, 228(2-3), 124-134 (2006-09-30)
(+/-)-2-Chloropropionic acid (2-CPA) is a neurotoxic compound which kills cerebellar granule cells in vivo, and makes cerebellar granule cells in vitro produce reactive oxygen species (ROS). We have studied the effect of 2-CPA on ROS formation in human neutrophil granulocytes
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