401-67-2 | Difluoroacetic anhydride

CAS:401-67-2 | Difluoroacetic anhydride ,Description

Difluoroacetic anhydride (DFA) is a chemical compound commonly used in organic synthesis. It is a colorless, volatile, and flammable liquid that has a sweet, pungent odor. It is a versatile reagent and has been used in a variety of reactions, including the synthesis of pharmaceuticals, natural products, and other compounds. DFA is also used in the production of a wide range of other compounds, including polymers, dyes, and fragrances. In addition, DFA has been studied for its potential use in medical and environmental applications.
 

Scientific Research Applications

Synthesis of Isoxazoles

Difluoroacetic anhydride plays a crucial role in the synthesis of isoxazoles. Lin, Wu, and Weng (2020) developed an efficient method using difluoroacetic anhydride for the synthesis of 5-difluoromethyl and 5-chlorodifluoromethyl isoxazoles. This process involves difluoroacetylation of vinyl azides, followed by deprotonation, cyclization, and dinitrogen elimination, achieving yields up to 89% (Lin, Wu, & Weng, 2020).

Gas Chromatography

In the field of gas chromatography, difluoroacetic anhydride is used in analyzing protein amino acids. Hušek (1982) described a method combining 1,3-dichlorotetrafluoroacetone with reactive anhydrides like heptafluorobutyric anhydride for a sensitive analysis of amino acids by gas chromatography (Hušek, 1982) .

Carbohydrate Chemistry

Trifluoroacetic anhydride, a closely related compound, finds application in carbohydrate chemistry. Bonner (1962) discussed its use in attempting to prepare cellulose trifluoroacetates, leading to the formation of chloroform-soluble products (Bonner, 1962).

Heterocyclic Chemistry

In heterocyclic chemistry, trifluoroacetic anhydride is employed for rearranging heterocyclic N-oxides. Daeniker and Druey (1958) demonstrated its use in obtaining compounds like 2-cyanoquinol-4-one from 2-cyanoquinoline N-oxide (Daeniker & Druey, 1958).

Esterification of Alcohols

Hudlický (1971) highlighted the use of trifluoroacetic anhydride for esterifying alcohols that are either too acidic or sterically hindered. It helps in converting organic acids to mixed anhydrides which are easily cleaved (Hudlický, 1971) .

Acylation of Aryl Methyl Ketones

Trifluoroacetic anhydride is used as an activator in the acylation of aryl methyl ketones. Shokova, Tafeenko, and Kovalev (2020) demonstrated its efficiency in producing β-diketones (Shokova, Tafeenko, & Kovalev, 2020).

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