234443-21-1 | 4-Bromo-3,3,4,4-tetrafluorobutan-1-ol

CAS:234443-21-1 | 4-Bromo-3,3,4,4-tetrafluorobutan-1-ol ,Description

4-Bromo-3,3,4,4-tetrafluorobutan-1-ol (4-Br-TBT) is an organic compound that is used in a variety of scientific research applications. It is a colorless, volatile liquid with a boiling point of about 27°C and a melting point of about -50°C. 4-Br-TBT is a versatile reagent that is used in organic synthesis, biochemistry, and pharmacology. This compound has a wide range of applications in both academic and industrial research.
 

Scientific Research Applications

Synthesis and Chemical Reactions

• Synthesis of Tetrafluorinated Aryl-C-Nucleosides: Enantioenriched tetrafluorinated aryl-C-nucleosides were synthesized from 1-benzyloxy-4-bromo-3,3,4,4-tetrafluorobutan-2-ol. The tetrafluorinated ethylene group in this synthesis is compatible with O-phosphorylation of the primary alcohol, as demonstrated in the preparation of tetrafluorinated naphthyl-C-nucleotide (Bonnac et al., 2010).
• Creation of Tetrafluoroethylene-containing Acetylene Derivatives: 4-Bromo-3,3,4,4-tetrafluorobut-1-ene was used to prepare lithium acetylide, which reacts with aldehydes, ketones, or chlorosilanes to produce acetylene derivatives. These derivatives underwent Diels–Alder reaction to afford multi-substituted benzene derivatives with a tetrafluoroethylene group (Konno et al., 2020).
• Generation of Halogenated Enolates for Synthesis: Chlorination/fluorination of aromatic trifluoroacetylated ketones using 4-bromo-3,3,4,4-tetrafluorobutan-1-ene led to the synthesis of ketones and alkenes exhibiting a terminal bromochlorofluoromethyl group. These products can be utilized in various chemical reactions (Balaraman et al., 2016).
• Fluorinated Material Synthesis: The compound is used in Heck reactions and Suzuki-Miyaura cross-coupling reactions to create multisubstituted alkenes bearing a tetrafluoroethylene fragment. This process yields structurally unique fluorinated materials (Sakaguchi et al., 2017).

Biological and Pharmaceutical Applications

• Palladium-Catalyzed Reactions in Anilides: 4-Bromo-3,3,4,4-tetrafluorobutene, with its -CF2CF2Br functional group, was used in a palladium-catalyzed olefination of anilides. This method is significant for synthesizing bioactive compounds, demonstrating the compound's utility in pharmaceutical synthesis (Wang et al., 2021).
• Stereochemical Analysis in Microbial Epoxidation: The compound was used in a study investigating the stereochemical course of microbial epoxidation. This research provides insight into the synthesis of stereochemically complex organic molecules, which can be crucial in the development of pharmaceutical compounds (Archelas et al., 1988).

Material Science and Polymer Chemistry

• Copolymerization with Hexafluoropropene Oxide: 4-Bromoheptafluoro-1,2-epoxybutanes, synthesized from 4-bromo-3,3,4,4-tetrafluorobutan-1-ol, were copolymerized with hexafluoropropene oxide. This demonstrates its use in creating specialized polymers and materials (Ito et al., 1979).
• Synthesis of Fluorinated Monomers for Copolymerization: The compound was used in the synthesis of bromofluorinated alkene, which was then copolymerized with vinylidene fluoride. This research indicates its potential in the development of novel polymers with specific properties (Guiot et al., 2005).

More Information