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559091

Sigma-Aldrich

Ethyl (2-chlorobenzoyl)acetate

≥95%

Synonym(s):

Ethyl (o-chlorobenzoyl)acetate, Ethyl 3-(2-chlorophenyl)-3-oxopropanoate, NSC 158136

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About This Item

Linear Formula:
ClC6H4COCH2CO2C2H5
CAS Number:
19112-35-7
Molecular Weight:
226.66
MDL number:
MFCD03424811
UNSPSC Code:
12352100
PubChem Substance ID:
24879794
NACRES:
NA.22

Quality Level

100

Assay

≥95%

refractive index

n20/D 1.540 (lit.)

bp

221-222 °C (lit.)

density

1.206 g/mL at 25 °C (lit.)

functional group

chloro
ester
ketone

SMILES string

CCOC(=O)CC(=O)c1ccccc1Cl

InChI

1S/C11H11ClO3/c1-2-15-11(14)7-10(13)8-5-3-4-6-9(8)12/h3-6H,2,7H2,1H3

InChI key

DLFBNTUSDQSFOF-UHFFFAOYSA-N

Application

Ethyl (2-chlorobenzoyl)acetate may be used to synthesize ketosplitomicin derivative and ethyl 6-(2-chlorophenyl)-2,2-dimethyl-4-oxo-2,3-dihydro-4Hpyran-5-carboxylate.
Reactant for:
  • Cerium ammonium nitrate-mediated oxidative coupling
  • Hydrosilylation reactions
  • Preparation of diaryl-substituted pyrazoles as potent CCR2 receptor antagonists
  • Preparation of potential herbicidal agents
  • Ruthenium-catalyzed asymmetric hydrogenation

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBS5552V
MKBL3807V
MKBK1142V
MKBJ5651V
MKBH7989V

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Characterization of sirtuin inhibitors in nematodes expressing a muscular dystrophy protein reveals muscle cell and behavioral protection by specific sirtinol analogues.
Pasco MY, et al.
Journal of Medicinal Chemistry, 53(3), 1407-1411 (2009)
Simple access to 5-carboalkoxy-2, 3-dihydro-4H-pyran-4-ones via domino acylative electrocyclization: the first three step total synthesis of the dihydronaphthopyran-4-one class of natural products.
Ilangovan A and Sakthivel P.
Royal Society of Chemistry Advances, 4(98), 55150-55161 (2014)

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