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Sigma-Aldrich

(R)-(+)-2-Chloropropionic acid

99%

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About This Item

Linear Formula:
CH3CH(Cl)CO2H
CAS Number:
7474-05-7
Molecular Weight:
108.52
Beilstein:
1720258
MDL number:
MFCD00064204
UNSPSC Code:
12352101
PubChem Substance ID:
24858501
NACRES:
NA.22

Assay

99%

form

liquid

optical activity

[α]20/D +14°, neat

refractive index

n20/D 1.4345 (lit.)

bp

185-188 °C (lit.)

density

1.258 g/mL at 20 °C (lit.)

functional group

carboxylic acid
chloro

SMILES string

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

InChI

1S/C3H5ClO2/c1-2(4)3(5)6/h2H,1H3,(H,5,6)/t2-/m1/s1

InChI key

GAWAYYRQGQZKCR-UWTATZPHSA-N

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Application

(R)-(+)-2-Chloropropionic acid can be used as a starting material in the synthesis of:       
  • Thiolactic acid, a key intermediate, which is used for the preparation of 2(R),5(S)-oxathiolanones by reacting with pivalaldehyde.       
  • (R)-2-chloropropionyl chloride, a key intermediate, which is utilized in the synthesis of (R)-4,5-dihydro-5-methylpyridazin-3(2H)-one derivative with pyrazolopyridine ring as a potential phosphodiesterase inhibitor.       
  • 2-Chloropropionamide derivatives as protein disulfide isomerase (PID) inhibitors.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1A

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

213.8 °F - closed cup

Flash Point(C)

101 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBK6784
STBK0305
STBH1357
STBG7987
STBB8446V

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Dharmaraja Allimuthu et al.
ACS chemical biology, 12(8), 2124-2131 (2017-06-15)
Resurgent interest in covalent target engagement in drug discovery has demonstrated that small molecules containing weakly reactive electrophiles can be safe and effective therapies. Several recently FDA-approved drugs feature an acrylamide functionality to selectively engage cysteine side chains of kinases
A short and efficient synthesis of a chiral pyridazinone derivative by the chiral-pool method
Yoshida N, et al.
Synthesis, 2004(10), 1554-1556 (2004)
Jill M McFadden et al.
Organic letters, 4(22), 3859-3862 (2003-02-26)
[formula: see text] A new and efficient asymmetric synthesis of naturally occurring (5R)-thiolactomycin (1) using D-alanine as the source of chirality is described.
Eugénie Grigorian et al.
Frontiers in microbiology, 12, 725997-725997 (2021-10-09)
L-2-halocid dehalogenases (L-2-HADs) have been mainly characterized from terrestrial polluted environments. By contrast, knowledge is still scarce about their role in detoxification of predominant halocarbons in marine environments. Here, phylogenetic analyses showed a wide diversity of homologous L-2-HADs, especially among

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