All Photos(1)
Synonym(s):
(Trifluoromethyl)trimethylsilane, Ruppert’s Reagent, TFMTMS
Linear Formula:
(CH3)3SiCF3
CAS Number:
Molecular Weight:
142.19
Beilstein:
4241868
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Quality Level
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Flam. Liq. 2 - Water-react 2
WGK
WGK 3
Flash Point(F)
1.4 °F
Flash Point(C)
-17 °C
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
危险化学品
Certificates of Analysis (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)
G K Surya Prakash et al.
The Journal of organic chemistry, 71(18), 6806-6813 (2006-08-26)
Organofluorine compounds are becoming increasingly important in different fields, such as material science, agro chemistry, and the pharmaceutical industry. Nucleophilic trifluoromethylation is one of the widely used methods to incorporate a trifluoromethyl moiety into organic molecules. We have carried out
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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