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B20347 (Trifluoromethyl)trimethylsilane, 98%

CAS Number
81290-20-2
Synonyms
Ruppert's Reagent
TFMTMS

Stock No. Size Price ($) Quantity Availability
B20347-03 1g 37.90
B20347-06 5g 121.00
B20347-14 25g 420.00
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(Trifluoromethyl)trimethylsilane, 98%

MDL
MFCD00145454
EINECS
000-000-0

Chemical Properties

Formula
C4H9F3Si
Formula Weight
142.20
Boiling Point
54-55°
Flash Point
-10°(14°F)
Density
0.962
Refractive Index
1.3305
Storage & Sensitivity
Moisture Sensitive. Ambient temperatures.
Solubility
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.

Literature References

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).

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H315-H319-H335

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

Precautionary Statements: P210-P233-P235-P240-P241-P242-P243-P261-P264b-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P363-P370+P378q-P501c

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Keep container tightly closed. Keep cool. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Use only non-sparking tools. Take precautionary measures against static discharge. Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Wash contaminated clothing before reuse. In case of fire: Use CO2, dry chemical, or foam Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
4241868
Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2931.90
TSCA
No

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