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(Trifluoromethyl)trimethylsilane

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(Trifluoromethyl)trimethylsilane Basic information

Product Name:
(Trifluoromethyl)trimethylsilane
Synonyms:
  • TriMethyl(trifluoroMethyl)silane solution 0.5 M in THF
  • (TrifluoroMethyl)triMethylsilane SynonyMs TriMethyl(trifluoroMethyl)silane
  • Ruppert-Prakash reagent
  • (Trimethylsilyl)trifluoromethane Ruppert-Prakash Reagent
  • Reagents, Ruppert's
  • TriMethylsilyl(trifluoroMethyl)silane
  • TriMethyl(trifluoroMethyl)sila
  • TriMethyl(trifluoroMethyl)silane 99%
CAS:
81290-20-2
MF:
C4H9F3Si
MW:
142.2
Product Categories:
  • C-C Bond Formation
  • organosilicon compounds
  • Fluorinated Building Blocks
  • Fluorinating Reagents & Building Blocks for Fluorinated Biochemical Compounds
  • Si (Classes of Silicon Compounds)
  • Si-(C)4 Compounds
  • Silicon Compounds (for Synthesis)
  • Synthetic Organic Chemistry
  • Chemical Synthesis
  • Fluorination Reagents
  • Organometallic Reagents
  • Organosilicon
  • Others
  • Ruppert's Reagent
  • Synthetic Reagents
  • Trifluoromethylation
Mol File:
81290-20-2.mol
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(Trifluoromethyl)trimethylsilane Chemical Properties

Boiling point:
54-55 °C (lit.)
Density 
0.962 g/mL at 20 °C (lit.)
vapor pressure 
10.98 psi ( 55 °C)
refractive index 
n20/D 1.386
Flash point:
14 °F
storage temp. 
2-8°C
solubility 
sol THF, ether, CH2Cl2.
form 
Liquid
color 
Clear colorless
Specific Gravity
0.962
Water Solubility 
Soluble in alcohol, THF, ether, dichloromethane, aromatic and aliphatic hydrocarbons. Soluble in water(with white smokes).
Sensitive 
Moisture Sensitive
Hydrolytic Sensitivity
4: no reaction with water under neutral conditions
Merck 
14,9683
BRN 
4241868
Exposure limits
ACGIH: TWA 50 ppm; STEL 100 ppm (Skin)
OSHA: TWA 200 ppm(590 mg/m3)
NIOSH: IDLH 2000 ppm; TWA 200 ppm(590 mg/m3); STEL 250 ppm(735 mg/m3)
InChIKey
MWKJTNBSKNUMFN-UHFFFAOYSA-N
CAS DataBase Reference
81290-20-2(CAS DataBase Reference)
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Safety Information

Hazard Codes 
F,Xi,Xn
Risk Statements 
11-36/37-19-36/37/38-22-40-14
Safety Statements 
16-33-39-26-36-29-36/37
RIDADR 
UN 1993 3/PG 2
WGK Germany 
3
10-21
Hazard Note 
Flammable
TSCA 
No
HazardClass 
3
PackingGroup 
II
HS Code 
29319090

MSDS

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(Trifluoromethyl)trimethylsilane Usage And Synthesis

Chemical Properties

(Trifluoromethyl)trimethylsilane (TMSCF3) is a flammable colorless liquid with a boiling point of 54–55 °C, a flash point of –17 °C and density of 0.926 g/mL at 20 °C. It is a trifluoromethylation reagent used in nucleophilic addition reactions of aldehydes and ketones. It may be harmful if inhaled, swallowed, absorbed through skin and may cause respiratory tract, skin and eye irritation. TMSCF3 was firstly synthesized by Rupert in 1984 via the condensation reaction of CF3Br and TMSCl with (Et2N)3P.

Uses

TMSCF3 is versatile reagent for trifluoromethylation, such as transition-metal-catalyzed reaction, miscellaneous trifluoromethylation, and addition to carbonyl and imine groups. These reactions are extremely useful approaches in the pharmaceutical and agrochemical industry, because they enhance metabolic stability (metabolic blocking) and alter the compound properties (liphophilicity, binding selectivity).

Uses

Silicon-based fluorinating reagents for the efficient trifluoromethylation of carbonyls and ethylene diamines. Precursors used for metal-mediated trifluoromethylation of aromatic, heteroaromatic, vinyl substrates, etc.

Preparation

(Trifluoromethyl)trimethylsilane is prepared from trimethylsilyl chloride and bromotrifluoromethane in the presence of a phosphorus(III) reagent that serves as a halogen acceptor.

General Description

Trimethyl(trifluoromethyl)silane (TMSCF3) is also called as Ruppert-Prakash fluorination reagent. It is extensively used for the synthesis of trifluoromethyl-containing compounds.

Purification Methods

Purify it by distilling it from trap to trap in a vacuum of 20mm using a bath at 45o and Dry-ice/Me2CO bath for the trap. The liquid in the trap is then washed with ice cold H2O (3x), the top layer is collected, dried (Na2SO4), and the liquid is decanted and fractionated through a helices-packed column at atmospheric pressure. 1H, 1 3C, 1 9F, and 2 9Si NMR can be used for assessing the purity of fractions. [Ruppert et al. Tetrahedron Lett 25 2195 1984, Krishnamurti et al. J Org Chem 56 984 199, Beilstein 4 IV 3892.]

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