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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:
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.)

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

Signal Word

Danger

Hazard Statements

H225,H261

Hazard Classifications

Flam. Liq. 2 - Water-react 2

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

1.4 °F - closed cup

Flash Point(C)

-17 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG6515
BCCF0617
BCCB4821
BCBW9275
BCBV1411

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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
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
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)
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