40556-44-3

Basic information

• Product Name: TFAD
• Synonyms: TrifluoroMethyl adaMantane;1-(Trifluoromethyl)adamantane;TFAD
• CAS NO: 40556-44-3
• Molecular Formula: C11H15F3
• Molecular Weight: 204.2320096
• Mol File: 40556-44-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 188.1±35.0 °C(Predicted)
• Appearance: /
• Density: 1.220±0.06 g/cm3(Predicted)
• CAS DataBase Reference: TFAD(CAS DataBase Reference)
• NIST Chemistry Reference: TFAD(40556-44-3)
• EPA Substance Registry System: TFAD(40556-44-3)

Safety Data

• Hazardous Substances Data: 40556-44-3(Hazardous Substances Data)

Usage

General Description

TFAD, or Trifluoroacetic acid deuterated, is a type of acid that is characterized by its high acidity and solubility in organic solvents. This chemical is commonly used as a reagent in various scientific experiments and processes, including organic synthesis. It is also used in analytical procedures such as proton nuclear magnetic resonance spectroscopy. Its chemical formula is CF3CDO2D. Although it is a crucial tool in many laboratory settings, TFAD is considered hazardous and needs to be handled with caution due to its potential skin corrosivity and harmful environmental effects.

Upstream product

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

Downstream Products

• 60096-00-6 perfluoro 1-methyladamantane 

Relevant articles and documents

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.

Syntheses and 13C NMR spectroscopic investigations of trifluoromethyl-substituted adamantanes

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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.