Ethyl 2,2-difluoro-3-oxobutanoate

Base Information

• Chemical Name: Ethyl 2,2-difluoro-3-oxobutanoate
• CAS No.: 2266-48-0
• Molecular Formula: C6H8F2O3
• Molecular Weight: 166.125
• Hs Code.: 2918300090
• DSSTox Substance ID: DTXSID00427056
• Nikkaji Number: J1.443.202G
• Wikidata: Q72463589
• Mol file: 2266-48-0.mol

Synonyms:2266-48-0;ETHYL 2,2-DIFLUORO-3-OXOBUTANOATE;Ethyl 2,2-difluoroacetoacetate;Butanoic acid, 2,2-difluoro-3-oxo-, ethyl ester;2,2-DIFLUORO-3-OXO-BUTYRIC ACID ETHYL ESTER;2,2-DIFLUORO-3-OXOBUTYRIC ACID ETHYL ESTER;SCHEMBL125138;DTXSID00427056;NXMSOLWESKBEJJ-UHFFFAOYSA-N;MFCD00190633;AKOS005207272;ETHYL2,2-DIFLUORO-3-OXOBUTANOATE;Ethyl 2,2-difluoroacetoacetate, AldrichCPR;A4842;AM20080913;FT-0625882;EN300-153092;AMINOTRI(METHYLENEPHOSPHONICACID)PENTASODIUMSALT

Chemical Property of Ethyl 2,2-difluoro-3-oxobutanoate

Chemical Property:

• Vapor Pressure: 2.3mmHg at 25°C
• Refractive Index: 1.4070
• Boiling Point: 161.2 °C at 760 mmHg
• Flash Point: 50.5 °C
• PSA: 43.37000
• Density: 1.194 g/cm³
• LogP: 0.77380
• Storage Temp.: 2-8°C
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 166.04415044
• Heavy Atom Count: 11
• Complexity: 177

Purity/Quality:

99% ^*data from raw suppliers

Ethyl2,2-difluoro-3-oxobutanoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:Flammable.; R36/38:Irritating to eyes and skin.
• Hazard Codes: R10:Flammable.; R36/38:Irritating to eyes and skin.
• Statements: 10-36/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C(=O)C)(F)F

Technology Process of Ethyl 2,2-difluoro-3-oxobutanoate

There total 3 articles about Ethyl 2,2-difluoro-3-oxobutanoate 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: 10.0%

ethyl acetoacetate (141-97-9) → ethyl-2-fluoroacetoacetate (1522-41-4) + 2,2-difluoro-3-oxobutyric acid ethyl ester (2266-48-0) + ethyl 2,4-difluoro-3-oxobutanoate (363-77-9)

Guidance literature:

With fluorine; In formic acid; at 10 - 15 ℃;

DOI:10.1016/0040-4020(95)00883-A

Reference yield:

ethyl acetoacetate (141-97-9) → ethyl-2-fluoroacetoacetate (1522-41-4) + 2,2-difluoro-3-oxobutyric acid ethyl ester (2266-48-0)

Guidance literature:

With 1-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate; zinc(II) chloride; In 1,2-dichloro-ethane; at 60 ℃; for 24h;

DOI:10.1021/ja00179a047

Reference yield:

[bis(acetoxy)iodo]benzene (3240-34-4) + ethyl acetoacetate (141-97-9) → ethyl-2-fluoroacetoacetate (1522-41-4) + 2,2-difluoro-3-oxobutyric acid ethyl ester (2266-48-0) + 2-acetoxy-acetoacetic acid ethyl ester (18632-42-3)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In acetonitrile; at 75 ℃; for 20h; Temperature; Inert atmosphere;

DOI:10.1002/ejoc.201500370

upstream raw materials:

ethyl acetoacetate

[bis(acetoxy)iodo]benzene

Downstream raw materials:

1-methyl-3-difluoromethyl-5-hydroxy-1H-pyrazole

Refernces

• 1、 Frantz, Richard,Hintermann, Lukas,Perseghini, Mauro,Broggini, Diego,Togni, Antonio. "Titanium-catalyzed stereoselective geminal heterodihalogenation of β-ketoesters". . p. 1709 - 1712. Retrieved 2007/10/03.
• 2、 Chambers, Richard D.,Greenhall, Martin P.,Hutchinson, John. "Direct Fluorination of 1,3-Dicarbonyl Compounds". . p. 21 - 22. Retrieved 2007/10/02.