2266-48-0

Basic information

• Product Name: ETHYL 2,2-DIFLUOROACETOACETATE
• Synonyms: 2,2-difluoro-acetoaceticacidethylester;ETHYL 2,2-DIFLUOROACETOACETATE;2,2-DIFLUORO-3-OXO-BUTYRIC ACID ETHYL ESTER;ETHYL 2,2-DIFLUOROACETOACETATE: TECH., 90%;Ethyl 2,2-difluoro-3-oxobutanoate;Butanoic acid, 2,2-difluoro-3-oxo-, ethyl ester
• CAS NO: 2266-48-0
• Molecular Formula: C₆H₈F₂O₃
• Molecular Weight: 166.12
• EINECS: -0
• Mol File: 2266-48-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 162°C
• Flash Point: 162°C
• Appearance: /
• Density: 1.194 g/cm³
• Vapor Pressure: 2.3mmHg at 25°C
• Refractive Index: 1.4070
• Storage Temp.: 2-8°C
• BRN: 1769592
• CAS DataBase Reference: ETHYL 2,2-DIFLUOROACETOACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 2,2-DIFLUOROACETOACETATE(2266-48-0)
• EPA Substance Registry System: ETHYL 2,2-DIFLUOROACETOACETATE(2266-48-0)

Safety Data

• Statements: 10-36/38
• Safety Statements: 16-26-36
• RIDADR: 1993
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 2266-48-0(Hazardous Substances Data)

Usage

General Description

ETHYL 2,2-DIFLUOROACETOACETATE, also known as ethyl 2,2-difluoro-3-oxo-butanoate, is a chemical compound with the molecular formula C6H8F2O3. It is a colorless liquid with a fruity odor, commonly used as an intermediate in the synthesis of pharmaceuticals and agrochemicals. ETHYL 2,2-DIFLUOROACETOACETATE is a fluorinated analog of ethyl acetoacetate and is used as a building block in the production of various fluorine-containing compounds. It is also used as a reagent in organic synthesis, particularly in the preparation of fluorine-containing molecules.ETHYL 2,2-DIFLUOROACETOACETATE is known to be a skin and eye irritant and should be handled with care.

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

Upstream product

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

Downstream Products

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

Relevant articles and documents

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.

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

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.