667-27-6 | Ethyl bromodifluoroacetate

CAS:667-27-6 | Ethyl bromodifluoroacetate ,Description

Ethyl bromodifluoroacetate (EBDF) is an organofluorine compound with a wide range of applications in the scientific and industrial fields. EBDF is a colorless, volatile liquid with a boiling point of 41.3 °C and a melting point of -30.3 °C. It is a versatile reagent used in the synthesis of pharmaceuticals, agrochemicals, and other organic compounds. EBDF is also used as a catalyst in the production of polymers and as a reactant in the manufacture of fluorinated polymers.
 

Scientific Research Applications

Copper-Catalyzed N-Formylation of Amines

Ethyl bromodifluoroacetate has been used as an N-formylating reagent in copper-catalyzed N-formylation of amines. This process is efficient for primary, secondary, cyclic arylamines, and aliphatic amines, providing N-formamides in moderate-to-excellent yields (Li et al., 2018).

Rhodium-Catalyzed Reformatsky-Type Reaction

This compound is effective in the Reformatsky-type reaction with carbonyl compounds, conducted in the presence of RhCl(PPh3)3, yielding β-hydroxy-α,α-difluoro carboxylic acid ethyl ester products (Sato et al., 2004).

1,4-Addition Reaction with Michael Acceptors

Ethyl bromodifluoroacetate reacts with Michael acceptors to form 1,4-adducts exclusively, enhancing the reaction's efficiency and simplifying the work-up process (Sato et al., 2003).

Synthesis of Compounds Containing CF2 Group

The reaction of ethyl bromodifluoroacetate in the presence of copper powder is used for synthesizing compounds containing a CF2 group. This method has been applied to synthesize various products, including cross-coupling products and radical addition products (Sato et al., 2004).

Triple Mode of Alkylation

Ethyl bromodifluoroacetate exhibits a triple mode of chemical reactivity, including N, O-Difluoromethylation, N-Ethylation, and S-(ethoxycarbonyl)difluoromethylation. This diverse reactivity is dependent on nucleophilicity and the base used (Polley et al., 2018).

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