2266-48-0

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 2,2-DIFLUOROACETOACETATE is used as an intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of fluorine-containing drug molecules. The presence of fluorine can enhance the pharmacokinetic and pharmacodynamic properties of the resulting compounds, potentially improving their efficacy and safety profiles.
Used in Agrochemical Industry:
In the agrochemical sector, ETHYL 2,2-DIFLUOROACETOACETATE is utilized as an intermediate in the production of agrochemicals, including pesticides and herbicides. The incorporation of fluorine atoms can lead to improved chemical stability and biological activity, making these products more effective in agricultural applications.
Used in Organic Synthesis:
ETHYL 2,2-DIFLUOROACETOACETATE is used as a reagent in organic synthesis, particularly for the preparation of fluorine-containing molecules. Its role as a building block allows for the creation of a wide range of chemical compounds with potential applications in various industries, including materials science, specialty chemicals, and more.
Used in Research and Development:
In research and development settings, ETHYL 2,2-DIFLUOROACETOACETATE is employed for the exploration of new chemical reactions and the synthesis of novel fluorinated compounds. Its unique properties make it a valuable tool for advancing the understanding of fluorine chemistry and its applications in various fields.

InChI:InChI=1/C6H8F2O3/c1-3-11-5(10)6(7,8)4(2)9/h3H2,1-2H3

Upstream product

• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 141-97-9 ethyl acetoacetate 

Downstream Products

• 129922-58-3 1-methyl-3-difluoromethyl-5-hydroxy-1H-pyrazole 

Relevant academic research and scientific papers

Apparent electrophilic fluorination of 1,3-dicarbonyl compounds using nucleophilic fluoride mediated by PhI(OAc)2

The apparent electrophilic fluorination of 1,3-dicarbonyl compounds using Et3N·3HF as a nucleophilic fluoride source is reported. This reaction requires PhI(OAc)2 as oxidant and can be conducted safely in standard laboratory glassware. Alternative selectivity compared to Selectfluor was observed in some cases. This approach may reduce our reliance on difficult-to-handle fluorine gas and expensive electrophilic fluorinating agents derived from elemental fluorine. Mechanistic analysis related to the active fluorinating species and fluoride/acetate exchange is presented. The apparent electrophilic fluorination of 1,3-dicarbonyl compounds using Et3N·3HF mediated by the in-situ formation of PhIF2 from PhI(OAc)2 is reported. This can be performed safely in standard laboratory glassware, and this approach may reduce our reliance on difficult-to-handle fluorine gas and expensive electrophilic fluorinating agents derived from elemental fluorine.

Titanium-catalyzed stereoselective geminal heterodihalogenation of β-ketoesters

(Matrix presented) β-Ketoesters can be effectively monofluorinated with F-TEDA using CpTiCl3 as a catalyst. With the use of this catalyst, the extent of the competing difluorination does not reach 10%. [TiCl2(TADDOLato)] complexes catalyze the one-pot enantioselective heterodihalogenation of β-ketoesters with F-TEDA and NCS to afford α-chloro-α-fluoro-β-ketoesters in moderate to good yields. The sequence of addition of the halogenating agents determines the sense of chiral induction.

Direct fluorination of 1,3-dicarbonyl compounds

In acid media, 1,3-diketones and 1,3-keloesters can be fluorinated in high yield and often with high conversion mainly to the corresponding 2-fluoro- compounds. Diesters such as diethyl malonate do not react with fluorine under the same reaction conditions. The mechanism of these reactions has been investigated and while the identity of the electrophilic fluorinating species is uncertain, we believe that the essential features of the reaction pathway are understood. Copyright

Direct Fluorination of 1,3-Dicarbonyl Compounds

1,3-Dicarbonyls, such as 1,3-diketones and 1,3-ketoesters, react directly with elemental fluorine at room temperature to give the corresponding 2-fluoro- and, in some cases, 2,2-difluoro-compounds in high yield.

Power and structure-variable fluorinating agents. The N-fluoropyridinium salt system

The usefulness of the N-fluoropyridinium salt system as a source of fluorinating agents was examined by using substituted or unsubstituted N-fluoropyridinium triflates 1-11, N-fluoropyridinium salts possessing other counteranions 1a-d and 3a, and the counteranion-bound salts, N-fluoropyridinium-2-sulfonates 12 and 13. Electrophilic fluorinating power was found to vary remarkably according to the electronic nature of the ring substituents. This power increased as the electron density of positive nitrogen sites decreased, and this was correlated to the pKa values of the corresponding pyridines. By virtue of this variation, it was possible to fluorinate a wide range of nucleophilic substrates differing in reactivity. It is thus possible to fluorinate aromatics, carbanions, active methylene compounds, enol alkyl or silyl ethers, vinyl acetates, ketene silyl acetals, and olefins through the proper use of salts pentachloro 6 through 2,4,6-trimethyl 2, their power decreasing in this order. All the reactions could be explained on the basis of a one-electron-transfer mechanism. N-Fluoropyridinium salts showed high chemoselectivity in fluorination, the extent depending on the reactive moiety. In consideration of these Findings, selective 9α-fluorination of steroids was carried out by reacting 1 with tris(trimethylsilyl ether) 73 of a triketo steroid. Regio- or stereoselectivity in fluorination was determined by a N-fluoropyridinium salt structure. Steric bulkiness of the N-F surroundings hindered the ortho fluorination of phenols and aniline derivatives, while the capacity for hydrogen bonding on the part of the counteranions prompted this process, and the counteranion-bound salts 12 and 13 underwent this fluorination exclusively or almost so. Both bulky N-fluoropyridinium triflates 2 and 7 preferentially attacked the 6-position of the conjugated vinyl ester of a steroid from the unhindered β-direction to give a thermally unstable 6β-fluoro isomer. On the basis of these results, N-fluoropyridinium salts may be concluded to constitute a system that can serve as a source of the most ideal fluorinating agents for conducting desired selective fluorination through fluorinating capacity or structural alteration.