It is employed as a valuable reagent for trifluoromethylation of electrophilic substrates. It is also use an the nucleophilic addition of the trifluoromethyl group to aldehydes and ketones. It generates trifluoromethide with catalytic amounts of F- (TBAF or CsF) and reacts with carbonyl compounds to produce trifluoromethylated alcohols.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
It is employed as a valuable reagent for trifluoromethylation of electrophilic substrates. It is also use an the nucleophilic addition of the trifluoromethyl group to aldehydes and ketones. It generates trifluoromethide with catalytic amounts of F- (TBAF or CsF) and reacts with carbonyl compounds to produce trifluoromethylated alcohols.
Solubility
Soluble in alcohol, THF, ether, dichloromethane, aromatic and aliphatic hydrocarbons. Soluble in water(with white smokes).
Notes
Moisture sensitive. Store away from oxidizing agents and water/moisture. Keep the container tightly closed and place it in a cool, dry and well ventilated condition. Store under inert gas.
RUO – Research Use Only
G K Surya Prakash, et al. Facile synthesis of TMS-protected trifluoromethylated alcohols using trifluoromethyltrimethylsilane (TMSCF3) and various nucleophilic catalysts in DMF.J Org Chem.2006,71(18), 6806-6813.
Rajendra P. Singh, et al.Cesium Fluoride Catalyzed Trifluoromethylation of Esters, Aldehydes, and Ketones with (Trifluoromethyl)trimethylsilane.J. Org. Chem.,1999,64(8), 2873-2876.
Valuable reagent for trifluoromethylation of electrophilic substrates.
In the presence of F-, aldehydes and ketones give, after hydrolysis of the intermediate silyl ethers, the trifluoromethyl carbinols: J. Am. Chem. Soc., 111, 393 (1989); J. Org. Chem., 56, 984 (1991); Org. Synth. Coll., 9, 711 (1998):
Alternatively, rapid and efficient trifluoromethylation of carbonyl compounds can be carried out at room temperature in DMSO, in the presence of molecular sieves, without fluoride or other basic catayst: Synlett, 112 (2006). The use of Tri-tert-butylphosphine, 10178 as a catalyst has also been advocated: Synlett, 267 (2006).
In the presence of CsF and TMS-imidazole, aldimines are converted to ɑ-trifluoromethyl amines: Tetrahedron Lett., 40, 5475 (1999).
With a catalytic amount of TBAF, excellent yields of trifluoromethyl ketones can be obtained from methyl esters: Angew. Chem. Int. Ed., 37, 820 (1998).
Similarly, alkyl or aryl thiocyanates are converted to the corresponding trifluoromethyl sulfides in generally good yields: Tetrahedron Lett., 38, 65 (1997). Selenocyanates behave similarly. Trifluoromethylation of aromatics bearing electron-withdrawing groups can be effected in the presence of KF, by displacement of nitro-, cyano- or chloro-substituents: J. Chem. Soc., Perkin 1, 3081 (1998).
For reviews of this and similar reagents, see: Chem. Rev., 97, 757 (1997); J. Fluorine Chem., 112, 123 (2001).