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306797

Sigma-Aldrich

(S)-(−)-2-Chloropropionic acid

99%

Synonym(s):

(S)-(−)-2-Chloropropanoic acid, L-α-Chloropropionic acid

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About This Item

Linear Formula:
CH3CH(Cl)CO2H
CAS Number:
29617-66-1
Molecular Weight:
108.52
Beilstein:
1720257
EC Number:
411-150-5
MDL number:
MFCD00064205
UNSPSC Code:
12352101
PubChem Substance ID:
24858499
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Assay

99%

form

liquid

optical activity

[α]25/D −14°, neat

refractive index

n20/D 1.4347 (lit.)

bp

77 °C/10 mmHg (lit.)

density

1.249 g/mL at 25 °C (lit.)

SMILES string

C[C@H](Cl)C(O)=O

InChI

1S/C3H5ClO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6)/t2-/m0/s1

InChI key

GAWAYYRQGQZKCR-REOHCLBHSA-N

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Application

(S)-(-)-2-Chloropropionic acid may be used in the preparation of (S)-(-)-2-chloropropionyl chloride[1] and DOTMA ([αR*(αR*,α′R*,α”R*,α”′R*)]-(α,α′,α”,α”′)-tetramethyl-1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid) ligand.[2]

Signal Word

Danger

Hazard Statements

H302 + H312,H314,H373

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1A - STOT RE 2

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

222.8 °F - closed cup

Flash Point(C)

106 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBP2576V
09508CW
14711MN
06626DY
04229JY

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Synthesis of optically pure. alpha.-alkylated. alpha.-amino acids and a single-step method for enantiomeric excess determination.
Kruizinga WH, et al.
The Journal of Organic Chemistry, 53(8) (1988)
A new ytterbium chelate as contrast agent in chemical shift imaging and temperature sensitive probe for MR spectroscopy.
Aime S, et al.
Magnetic Resonance in Medicine : Official Journal of the Society of Magnetic Resonance in Medicine / Society of Magnetic Resonance in Medicine, 35(5), 648-651 (1996)
Stephen Duffell et al.
Neurotoxicology, 25(6), 1031-1040 (2004-10-12)
Previous studies have shown that L-2-chloropropionic acid (L-CPA) produces necrosis to cerebellar granule cells with some associated Purkinje cell damage in the rat. We have re-evaluated the neuropathology using the original sections and fresh sections from archived brain material from
Atsushi Kurata et al.
The Journal of biological chemistry, 280(21), 20286-20291 (2005-03-23)
A soil bacterium, Burkholderia sp. WS, grows on 2-chloroacrylate as the sole carbon source. To identify the enzymes metabolizing 2-chloroacrylate, we carried out comparative two-dimensional gel electrophoresis of the proteins from 2-chloroacrylate- and lactate-grown bacterial cells. As a result, we
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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