Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate

Base Information

• Chemical Name: Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate
• CAS No.: 1999-00-4
• Molecular Formula: C11H11FO3
• Molecular Weight: 210.205
• Hs Code.: 29183000
• DSSTox Substance ID: DTXSID20374518
• Nikkaji Number: J31.453F
• Wikidata: Q72474932
• Mol file: 1999-00-4.mol

Synonyms:Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate;1999-00-4;Ethyl 4-fluorobenzoylacetate;Ethyl (4-fluorobenzoyl)acetate;4-Fluorobenzoylacetic acid ethyl ester;ETHYL 3-(4-FLUOROPHENYL)-3-OXOPROPIONATE;MFCD03093631;BENZENEPROPANOIC ACID, 4-FLUORO-BETA-OXO-, ETHYL ESTER;(4-Fluorobenzoyl)acetic Acid Ethyl Ester;ETHYL 3-(4'-FLUOROPHENYL)-3-OXOPROPANOATE;3-(4-FLUORO-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER;ethyl p-fluorobenzoylacetate;(P-FLUOROBENZOYL)ACETIC ACID ETHYL ESTER;SCHEMBL314260;DTXSID20374518;CS-M1528;ethyl 4-fluorophenyl-3-oxopropanoate;ETHYL(4-FLUOROBENZOYL)ACETATE;STK508806;AKOS000266022;ethyl3-(4-fluorophenyl)-3-oxopropanoate;AC-27327;AS-12159;BP-11732;SY008086;ethyl 3-oxo-3-(4-fluorophenyl)propionate;ethyl 3-(4-fluoro-phenyl)-3-oxo-propionate;F0435;FT-0633962;EN300-51105;ethyl beta-(p-fluorophenyl)-beta-oxopropionate;3-(4-Fluorophenyl)-3-oxo-propionic ethyl ester;3-(4--Fluorophenyl)-3-oxo-propionic ethyl ester;A814141;3-(4-fluorophenyl)-3-oxopropionic acid ethyl ester;4-Fluoro-beta-oxobenzenepropanoic acid, ethyl ester;W-201751;3-(4'-Fluorophenyl)-3-oxopropanoic acid, ethyl ester;F0871-0803

Chemical Property of Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 117-120℃
• Refractive Index: n20/D 1.5040(lit.)
• Boiling Point: 280.4 °C at 760 mmHg
• PKA: 9.82±0.25(Predicted)
• Flash Point: 119.6 °C
• PSA: 43.37000
• Density: 1.179 g/cm³
• LogP: 1.96160
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 210.06922237
• Heavy Atom Count: 15
• Complexity: 232

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl3-(4-Fluorophenyl)-3-oxopropanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(=O)C1=CC=C(C=C1)F
• Uses: Reactant used as a precursor in:Condensation reactions with diamines via C-C bond cleavage for synthesis of benzimidazoles and perimidines for possible use as antimalarial treatmentsBase-promoted domino Michael addition / cyclization / elimination reactions for synthesis of hydroxybenzophenonesOxidative cross-coupling with indoles via dioxygen activationCyclization of keto esters for synthesis of pyronesLewis base catalyzed hydrosilylation for synthesis of α-acetoxy β-amino acid derivativesConia-ene reactions for synthesis of methylenecyclopentane derivatives

Technology Process of Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate

There total 28 articles about Ethyl 3-(4-Fluorophenyl)-3-Oxopropanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1-(4-fluorophenyl)ethanone (403-42-9) + Diethyl carbonate (105-58-8,76619-83-5) → ethyl 3-(4'-fluorophenyl)-3-oxopropionate (1999-00-4)

Guidance literature:

With sodium hydride; In toluene; Heating;

Reference yield: 93.0%

ethyl-3-hydroxy-2-diazo-3-(4-fluorophenyl)-propanoate (442157-12-2) → ethyl 3-(4'-fluorophenyl)-3-oxopropionate (1999-00-4)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; In neat (no solvent); at 20 ℃; for 5h;

DOI:10.1039/c3ra41920g

Reference yield: 88.0%

4-fluoro-N-phenyl-N-tosylbenzamide + ethyl acetate (141-78-6) → ethyl 3-(4'-fluorophenyl)-3-oxopropionate (1999-00-4)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at 25 ℃; for 2h; chemoselective reaction; Inert atmosphere; Green chemistry;

DOI:10.1021/acs.joc.0c02868

upstream raw materials:

ethyl 2-(4-fluorobenzoyl)acetoacetate

1-(4-fluorophenyl)ethanone

Diethyl carbonate

4-fluorobenzoic acid ethyl ester

Downstream raw materials:

6-(4-fluoro-phenyl)-[1,3]oxazine-2,4-dione

5-(4-fluorophenyl)-1,2,4-triazolo<1,5-a>pyrimidin-7-ol

ethyl 1-(4'-fluorophenyl)-3-(dimethylamino)prop-2-enone-2-carboxylate

2-Amino-6-(4-fluoro-phenyl)-3H-pyrimidin-4-one

Refernces

• 1、 Lv, Xue-Jiao,Chen, Ying-Han,Liu, Yan-Kai. "Two Competitive but Switchable Organocatalytic Cascade Reaction Pathways: The Diversified Synthesis of Chiral Acetal-Containing Bridged Cyclic Compounds". . p. 190 - 195. Retrieved 2019.
• 2、 Hu, Wangcheng,He, Xinwei,Zhou, Tongtong,Zuo, Youpeng,Zhang, Shiwen,Yang, Tingting,Shang, Yongjia. "Construction of isoxazolone-fused phenanthridinesviaRh-catalyzed cascade C-H activation/cyclization of 3-arylisoxazolones with cyclic 2-diazo-1,3-diketones". supporting information. p. 552 - 556. Retrieved 2021/02/06.
• 3、 Roy, Sourav,Kumar, Gourav,Chatterjee, Indranil. "Photoinduced Diverse Reactivity of Diazo Compounds with Nitrosoarenes". supporting information. p. 6709 - 6713. Retrieved 2021/09/08.