40556-44-3

Usage

Uses

Used in Scientific Research:
TFAD is used as a reagent in various scientific experiments for its high acidity and solubility in organic solvents, facilitating organic synthesis and other chemical reactions.
Used in Analytical Procedures:
TFAD is used as a reagent in proton nuclear magnetic resonance (NMR) spectroscopy, a technique that helps in the identification and characterization of organic compounds by analyzing the magnetic properties of certain atomic nuclei.
Used in Organic Synthesis:
TFAD is used as a reagent in organic synthesis processes, where its high acidity and solubility in organic solvents contribute to the formation of desired chemical products.
Used in Laboratory Settings:
TFAD is used as a crucial tool in many laboratory settings, where its properties enable the execution of various chemical reactions and analyses, despite its hazardous nature that necessitates careful handling.

Upstream product

• 64-18-6 formic acid 
• 281-23-2 adamantane 
• 828-51-3 1-Adamantanecarboxylic acid 
• 40933-60-6 adamantane dicarboxylic acid 
• 768-90-1 1-Adamantyl bromide 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 10405-61-5 (3r,5r,7r)-adamantane-1-carbonyl fluoride 

Downstream Products

• 60096-00-6 perfluoro 1-methyladamantane 

Relevant academic research and scientific papers

Deoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD/Olah's reagent under solvent-free conditions

A new protocol enabling the formation of trifluoromethyl compounds from acyl fluorides has been developed. The combination of FLUOLEAD and Olah's reagent in solvent-free conditions at 70 °C initiated the significant deoxyfluorination of the acyl fluorides and resulted in the corresponding trifluoromethyl products with high yields (up to 99%). This strategy showed a great tolerance for various acyl fluorides containing aryloyl, (heteroaryl)oyl, or aliphatic acyl moieties, providing good to excellent yields of the trifluoromethyl products. Synthetic drug-like molecules were also transformed into the corresponding trifluoromethyl compounds under the same reaction conditions. A reaction mechanism is proposed.

Metallaphotoredox Perfluoroalkylation of Organobromides

Ruppert-Prakash type reagents (TMSCF3, TMSC2F5, and TMSC3F7) are readily available, air-stable, and easy-to-handle fluoroalkyl sources. Herein, we describe a mild, copper-catalyzed cross-coupling of these fluoroalkyl nucleophiles with aryl and alkyl bromides to produce a diverse array of trifluoromethyl, pentafluoroethyl, and heptafluoropropyl adducts. This light-mediated transformation proceeds via a silyl-radical-mediated halogen atom abstraction pathway, which enables perfluoroalkylation of a broad range of organobromides of variable steric and electronic demand. The utility of the method is demonstrated through the late-stage functionalization of several drug analogues.

Cyclic hydrocarbon perfluorination process

Perfluorinated polycyclic hydrocarbons may be produced in high yield by a three-stage process comprising contacting a cyclic hydrocarbon such as an alkyladamantane with a fluoride of silver, manganese, sulfur or the like under varying reaction conditions, generally in the liquid state, to provide a partially fluorinated cyclic hydrocarbon. This fluorination is followed by a second stage vapor phase reaction with a fluoride of cobalt or the like at temperatures generally just above the boiling point of the material to yield highly fluorinated cyclic compounds, followed by a third stage reaction with the same reagent at substantially higher temperatures to provide the desired perfluorinated material. Alternatively, the partially fluorinated material for use in the second stage may be derived from known sources, using any known partially fluorinated cyclic hydrocarbon. In a further embodiment, a fluidized bed reactor may be substituted for the second and third vapor phase stages described above.