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488712

Sigma-Aldrich

Trimethyl(trifluoromethyl)silane

99%

Synonym(s):

(Trifluoromethyl)trimethylsilane, Ruppert’s Reagent, TFMTMS

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About This Item

Linear Formula:
(CH3)3SiCF3
CAS Number:
81290-20-2
Molecular Weight:
142.19
Beilstein/REAXYS Number:
4241868
MDL number:
MFCD00145454
UNSPSC Code:
12352101
PubChem Substance ID:
24872418
NACRES:
NA.22

Quality Level

200

assay

99%

reaction suitability

reaction type: C-C Bond Formation

bp

54-55 °C (lit.)

density

0.962 g/mL at 20 °C (lit.)

functional group

fluoro

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL8659
BCCK8284
BCCH6480
BCCG6515
BCCF0617

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Copper-catalyzed aerobic oxidative trifluoromethylation of H-phosphonates using trimethyl (trifluoromethyl) silane
Chu L, et al.
Synthesis, 44(10), 1521-1525 (2012)
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
Stereoselective Nucleophilic Trifluoromethylation of N?(tert?Butylsulfinyl) imines by Using Trimethyl (trifluoromethyl) silane.
Prakash G K, et al.
Angewandte Chemie (International Edition in English), 113(3), 609-610 (2001)
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)
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
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