Ethyl 3-(3-chloro-2,4,5-trifluorophenyl)-3-oxopropanoate

Inquiry

Cat Number

INT101987864

CAS Number

101987-86-4

If you have any other questions, please contact our experts.

Product Detail Description Customer Q&A

CAS Number

101987-86-4

EINECS

1806241-263-5

Storage

Sealed in dry, room temperature

Synonyms

Ethyl 2-(3-chloro-2,4,5-trifluorobenzoyl)acetate; Ethyl 3-chloro-2,4,5-trifluorobenzoylacetate

Molecular Formula

C11H8ClF3O3

Molecular Weight

280.63

Smiles

C1(=CC(F)=C(F)C(Cl)=C1F)C(=O)CC(OCC)=O

Appearance

White to off-white solid

Melting Point

80-83℃

Boiling Point

325℃

Relative Density

1.413

pKa

10.32

General Description

Ethyl 3-(3-chloro-2,4,5-trifluorophenyl)-3-oxopropanoate is a highly functionalized beta-keto ester characterized by a polyfluorinated aromatic ring. This compound serves as a vital intermediate in the synthesis of advanced fluoroquinolone antibiotics. The presence of the chlorine atom at the 3-position and fluorine atoms at the 2, 4, and 5-positions of the phenyl ring provides a specific substitution pattern that is essential for the high potency and broad-spectrum activity of the resulting pharmaceutical compounds.

Mechanism of Action

As a synthetic building block, ethyl 3-(3-chloro-2,4,5-trifluorophenyl)-3-oxopropanoate functions as the core scaffold for the construction of the quinolone ring system. The beta-keto ester moiety is highly reactive, allowing for subsequent condensation reactions with amines and orthoesters to form the bicyclic heterocyclic structure characteristic of quinolone antibiotics. The specific halogenation pattern (chloro and trifluoro) is strategically designed to optimize the binding affinity to bacterial DNA gyrase and topoisomerase IV, while simultaneously enhancing the lipophilicity and cellular penetration of the final drug molecule.

Application

Ethyl 3-(3-chloro-2,4,5-trifluorophenyl)-3-oxopropanoate is primarily utilized as a key intermediate in the production of Sitafloxacin and other high-potency fluoroquinolones. It is employed in the manufacturing of active pharmaceutical ingredients (APIs) used to treat severe respiratory and urinary tract infections. It is also used in medicinal chemistry research to develop novel antibacterial agents and as a specialized reagent in organic synthesis to introduce polyfluorinated benzoyl groups into complex molecules.

What is the role of ethyl 3-(3-chloro-2,4,5-trifluorophenyl)-3-oxopropanoate in pharmaceutical synthesis?

It serves as the central scaffold for building the quinolone ring system in advanced antibiotics like Sitafloxacin.

What is the MOQ for ethyl 3-(3-chloro-2,4,5-trifluorophenyl)-3-oxopropanoate?

MOQs are flexible and can be adapted for research or industrial scale. Please contact our team for details.

Can ethyl 3-(3-chloro-2,4,5-trifluorophenyl)-3-oxopropanoate be used to synthesize other quinolones?

Yes, it is a versatile intermediate that can be adapted for the synthesis of various halogenated quinolone derivatives.

Are technical documents like COA and SDS available?

Yes, every batch is supplied with a batch-specific Certificate of Analysis.