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81290-20-2 - (Trifluoromethyl)trimethylsilane, 98% - Ruppert's Reagent - TFMTMS - B20347 - Alfa Aesar

B20347 (Trifluoromethyl)trimethylsilane, 98%

Codice CAS
Ruppert's Reagent

Dimensioni Prezzo ($) Quantità Disponibilità
1g 36,10
5g 115,00
25g 400,00
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(Trifluoromethyl)trimethylsilane, 98%


Proprietà chimiche

Peso formula
Punto di ebollizione
Punto di infiammabilità
Indice di rifrazione
Moisture Sensitive
Soluble in alcohol, THF, ether, dichloromethane, aromatic and aliphatic hydrocarbons. Soluble in water(with white smokes).


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.


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.


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).

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H225-H315-H319-H335

Highly flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Dichiarazioni precauzionali: P210-P261-P280-P240-P303+P361+P353-P305+P351+P338-P304+P340-P362-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Classe di rischio
Gruppo di imballaggio
Codice tariffe armonizzato


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