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

B20347 (Trifluoromethyl)trimethylsilane, 98%

Numéro CAS
81290-20-2
Synonymes
Ruppert's Reagent
TFMTMS

Dimensions Prix ($) Quantité Disponibilité
1g 36,46
5g 116,39
25g 355,68
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(Trifluoromethyl)trimethylsilane, 98%

MDL
MFCD00145454
EINECS
000-000-0

Propriétés chimiques

Formule
C4H9F3Si
Poids formulaire
142.20
Point d'ébullition
54-55°
Point d'éclair
-10°(14°F)
Densité
0.962
Indice de réfraction
1.3305
Sensibilité
Moisture Sensitive
Solubilité
Soluble in alcohol, THF, ether, dichloromethane, aromatic and aliphatic hydrocarbons. Soluble in water(with white smokes).

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.

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.

Références bibliographiques

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).

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H225-H315-H319-H335

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

Mentions de prudence: 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.

Autres références

Beilstein
4241868
Classe de danger
3
Groupe d'emballage
II
Code tarifaire harmonisé
2931.90
TSCA
No

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