Ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate

Base Information

• Chemical Name: Ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate
• CAS No.: 96568-04-6
• Molecular Formula: C10H8Cl2FNO3
• Molecular Weight: 280.083
• Hs Code.: 29333990
• DSSTox Substance ID: DTXSID4049379
• Nikkaji Number: J340.035B
• Wikidata: Q72474211
• ChEMBL ID: CHEMBL3185319
• Mol file: 96568-04-6.mol

Synonyms:ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate;Ethyl 3-(2,6-Dichloro-5-fluoro-3-pyridyl)-3-oxopropionate;ETHYL 2,6-DICHLORO-5-FLUORONICOTINOYLACETATE;DTXSID4049379;MFCD00799535;3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoic acid ethyl ester;Ethyl 2,6-dichloro-5-fluornicotinoylacetate;Ethyl 2,6-dichloro-5-fluoro-beta-oxo-3-pyridinepropionate;Ethyl2,6-dichloro-5-fluoropyridine-3-acetoacetate;SCHEMBL1389163;CHEMBL3185319;DTXCID1029338;(2,6-Dichloro-5-fluoronicotinoyl)acetic Acid Ethyl Ester;IEUHWNLWVMLHHC-UHFFFAOYSA-N;Tox21_202905;AKOS015838712;AC-7742;AS-9195;NCGC00260451-01;BP-12689;SY050796;CAS-96568-04-6;CS-0059185;E0811;FT-0625980;Ethyl (2,6-Dichloro-5-fluoronicotinoyl)acetate;J-520797;Ethyl 2,6-dichloro-5-fluoro-?-oxo-3-pyridinepropionate;Ethyl3-(2,6-Dichloro-5-fluoro-3-pyridyl)-3-oxopropionate;Ethyl 2,6-dichloro-5-fluoro- beta -oxo-3-pyridinepropionate;Ethyl 3-(2,6-dichloro-5-fluoro-3-pyridinyl)-3-oxopropanoate;ethyl 3-(2,6-dichloro-5-fluoro-3-pyridyl)-3-oxopropanoate;ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxo-propanoate;Ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxo-propionate;beta-Oxo-2,6-dichloro-5-fluoropyridine-3-propanoic acid ethyl ester;Ethyl 2,6-dichloro-5-fluoro-beta-oxo-3-pyridinepropionate, 98%;3-(2,6-Dichloro-5-fluoro-3-pyridyl)-3-oxopropionic Acid Ethyl Ester

Chemical Property of Ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate

Chemical Property:

• Appearance/Colour: Off-white powder
• Vapor Pressure: 4.57E-05mmHg at 25°C
• Melting Point: 68-72 °C(lit.)
• Refractive Index: 1.524
• Boiling Point: 349.9 °C at 760 mmHg
• PKA: 9.43±0.50(Predicted)
• Flash Point: 165.4 °C
• PSA: 56.26000
• Density: 1.434 g/cm³
• LogP: 2.59230
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 278.9865267
• Heavy Atom Count: 17
• Complexity: 303

Purity/Quality:

99% ^*data from raw suppliers

3-(2,6-Dichloro-5-fluoropyridin-3-yl)-3-oxopropanoicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)CC(=O)C1=CC(=C(N=C1Cl)Cl)F
• Uses: Enoxacin intermediate.

Technology Process of Ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate

There total 16 articles about Ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-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: 80.0%

ethyl potassium malonate (6148-64-7) + 2,6-dichloro-5-fluoro-pyridine-3-carbonitrile (82671-02-1) → ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate (96568-04-6)

Guidance literature:

ethyl potassium malonate; 2,6-dichloro-5-fluoro-pyridine-3-carbonitrile; With zinc(II) chloride; In 1,2-dichloro-ethane; Heating / reflux;

With hydrogenchloride; water; In 1,2-dichloro-ethane; at 90 ℃; for 4h; Product distribution / selectivity;

Reference yield: 70.0%

2-[1-(2,6-Dichloro-5-fluoro-pyridin-3-yl)-1-hydroxy-meth-(E)-ylidene]-3-oxo-butyric acid ethyl ester → ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate (96568-04-6)

Guidance literature:

With pyridinium p-toluenesulfonate; In ethanol; for 18h; Heating;

DOI:10.1080/00304949709355192

Reference yield: 48.0%

ethyl potassium malonate (6148-64-7) + 5-fluoro-2,6-dihydroxynicotinonitrile (113237-18-6) → ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxopropanoate (96568-04-6)

Guidance literature:

5-fluoro-2,6-dihydroxynicotinonitrile; With phosphorus pentachloride; trichlorophosphate; Heating / reflux;

ethyl potassium malonate; With zinc(II) chloride; In 1,2-dichloro-ethane; Heating / reflux;

With hydrogenchloride; water; In 1,2-dichloro-ethane; at 90 ℃; for 4h; Product distribution / selectivity;

upstream raw materials:

hydrogen ethyl malonate

2,6-dichloro-5-fluoro-3-nicotinoyl chloride

diethyl (ethoxymagnesio)malonate

ethyl potassium malonate

Downstream raw materials:

7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid

ethyl 3-p-fluoroanilino-2-(2,6-dichloro-5-fluoronicotinyl)acrylate

(Z)-2-(2,6-Dichloro-5-fluoro-pyridine-3-carbonyl)-3-phenylamino-acrylic acid ethyl ester

7-chloro-1-(2,4-dimethoxybenzyl)-6-fluoro-4-oxo-1,4-dihydro[1,8]naphthyridine-3-carboxylic acid ethyl ester

Refernces

• 1、 -. "ANTIVIRAL AND ANTIMICROBIAL COMPOUNDS". Paragraph 0128; 0130. . Retrieved 2014/03/25.
• 2、 -. "Process for Preparing Beta-Ketoester Compounds". Page/Page column 3. . Retrieved 2008/12/08.