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488712

Sigma-Aldrich

Trimethyl(trifluoromethyl)silane

99%

Sinónimos:

(Trifluoromethyl)trimethylsilane, Ruppert’s Reagent, TFMTMS

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About This Item

Fórmula lineal:
(CH3)3SiCF3
Número de CAS:
81290-20-2
Peso molecular:
142.19
Beilstein/REAXYS Number:
4241868
MDL number:
MFCD00145454
UNSPSC Code:
12352101
PubChem Substance ID:
24872418
NACRES:
NA.22

assay

99%

reaction suitability

reaction type: C-C Bond Formation

bp

54-55 °C (lit.)

density

0.962 g/mL at 20 °C (lit.)

storage temp.

2-8°C

SMILES string

C[Si](C)(C)C(F)(F)F

InChI

1S/C4H9F3Si/c1-8(2,3)4(5,6)7/h1-3H3

InChI key

MWKJTNBSKNUMFN-UHFFFAOYSA-N

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Application

Trimethyl(trifluoromethyl)silane can be used as a trifluoromethylating agent in the following processes:
  • Conversion of N-(tert-butylsulfinyl)-imines to trifluoromethylated amines
  • Conversion of trans-enones to trans-α-trifluoromethyl silyl ethers
  • Trifluoromethylation of azomethine imines
  • Conversion of H-phosphonates to CF3-phosphonates
  • Nucleophilic addition of the trifluoromethyl group to aldehydes and ketones.

pictograms

Flame
GHS02

signalword

Danger

hcodes

H225,H261

Hazard Classifications

Flam. Liq. 2 - Water-react 2

Storage Class

4.3 - Hazardous materials which set free flammable gases upon contact with water

wgk_germany

WGK 3

flash_point_f

1.4 °F - closed cup

flash_point_c

-17 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves

Certificados de análisis (COA)

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Craig P Johnston et al.
Journal of the American Chemical Society, 140(35), 11112-11124 (2018-08-07)
The mechanism of CF3 transfer from R3SiCF3 (R = Me, Et, iPr) to ketones and aldehydes, initiated by M+X- (<0.004 to 10 mol %), has been investigated by analysis of kinetics (variable-ratio stopped-flow NMR and IR), 13C/2H KIEs, LFER, addition
CsF-catalyzed nucleophilic trifluoromethylation of trans-enones with trimethyl (trifluoromethyl) silane: A facile synthesis of trans-?-trifluoromethyl allylic alcohols.
Singh R P, et al.
Organic Letters, 1(7), 1047-1049 (1999)
Copper-catalyzed aerobic oxidative trifluoromethylation of H-phosphonates using trimethyl (trifluoromethyl) silane
Chu L, et al.
Synthesis, 44(10), 1521-1525 (2012)
Catalytic enantioselective trifluoromethylation of azomethine imines with trimethyl (trifluoromethyl) silane
Kawai H, et al.
Angewandte Chemie (International Edition in English), 121(34), 6442-6445 (2009)
Peter T Kaplan et al.
Beilstein journal of organic chemistry, 13, 2297-2303 (2017-11-29)
A number of copper reagents were compared for their effectiveness in trifluoromethylating 4-iodobiphenyl, 4-iodotoluene, and 2-iodotoluene. Yields over time were plotted in order to refine our understanding of each reagent performance, identify any bottlenecks, and provide more insight into the
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