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Trimethyl(trifluoromethyl)silane

Base Information Edit
  • Chemical Name:Trimethyl(trifluoromethyl)silane
  • CAS No.:81290-20-2
  • Molecular Formula:C4H9F3Si
  • Molecular Weight:142.196
  • Hs Code.:29319090
  • UNII:A009786QPJ
  • DSSTox Substance ID:DTXSID20338998
  • Nikkaji Number:J357.229C
  • Wikipedia:Trifluoromethyltrimethylsilane
  • Wikidata:Q651896
  • Mol file:81290-20-2.mol
Trimethyl(trifluoromethyl)silane

Synonyms:(trifluoromethyl)-trimethylsilane;(trifluoromethyl)trimethylsilane;CF3SiMe3

Suppliers and Price of Trimethyl(trifluoromethyl)silane
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • Trimethylsilyl(trifluoromethane)
  • 100g
  • $ 225.00
  • TCI Chemical
  • (Trifluoromethyl)trimethylsilane [Trifluoromethylating Reagent] >97.0%(GC)
  • 25g
  • $ 82.00
  • TCI Chemical
  • (Trifluoromethyl)trimethylsilane [Trifluoromethylating Reagent] >97.0%(GC)
  • 5g
  • $ 27.00
  • SynQuest Laboratories
  • Trifluoromethyltrimethylsilane 99.0%
  • 500 g
  • $ 475.00
  • SynQuest Laboratories
  • (Trifluoromethyl)trimethylsilane, 0.5M in THF
  • 5 mL
  • $ 26.00
  • SynQuest Laboratories
  • Trifluoromethyltrimethylsilane 99.0%
  • 5 g
  • $ 15.00
  • SynQuest Laboratories
  • Trifluoromethyltrimethylsilane 99.0%
  • 25 g
  • $ 30.00
  • SynQuest Laboratories
  • (Trifluoromethyl)trimethylsilane, 0.5M in THF
  • 25 mL
  • $ 58.00
  • SynQuest Laboratories
  • Trifluoromethyltrimethylsilane 99.0%
  • 100 g
  • $ 95.00
  • SynQuest Laboratories
  • (Trifluoromethyl)trimethylsilane, 0.5M in THF
  • 100 mL
  • $ 136.00
Total 167 raw suppliers
Chemical Property of Trimethyl(trifluoromethyl)silane Edit
Chemical Property:
  • Appearance/Colour:clear colorless solution 
  • Vapor Pressure:10.98 psi ( 55 °C) 
  • Refractive Index:n20/D 1.386  
  • Boiling Point:49.3 °C at 760 mmHg 
  • Flash Point:-16 °C 
  • PSA:0.00000 
  • Density:0.969 g/cm3 
  • LogP:2.84600 
  • Storage Temp.:2-8°C 
  • Sensitive.:Moisture Sensitive 
  • Solubility.:sol THF, ether, CH2Cl2. 
  • Water Solubility.:Soluble in alcohol, THF, ether, dichloromethane, aromatic and aliphatic hydrocarbons. Soluble in water(with white smokes). 
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:3
  • Rotatable Bond Count:0
  • Exact Mass:142.04256131
  • Heavy Atom Count:8
  • Complexity:78.3
Purity/Quality:

99% *data from raw suppliers

Trimethylsilyl(trifluoromethane) *data from reagent suppliers

Safty Information:
  • Pictogram(s): FlammableF,HarmfulXn,IrritantXi 
  • Hazard Codes:F,Xi,Xn 
  • Statements: 11-36/37-19-36/37/38-22-40-14 
  • Safety Statements: 16-33-39-26-36-29-36/37 
MSDS Files:

SDS file from LookChem

Useful:
  • Canonical SMILES:C[Si](C)(C)C(F)(F)F
  • General Description (Trifluoromethyl)trimethylsilane (TMSCF3), also known as Ruppert's reagent, is a versatile nucleophilic trifluoromethylating agent widely used in organic synthesis. It reacts with carbonyl compounds, gem-difluoroalkenes, and benzoic acids under fluoride activation to introduce trifluoromethyl groups, enabling the synthesis of fluorinated alcohols, ketones, and complex organic molecules. Its applications span pharmaceuticals, agrochemicals, and material science due to its ability to form stable trifluoromethylated intermediates under mild, metal-free conditions. The reagent is particularly valuable for constructing non-hydrolyzable glycoside mimics and bioactive compounds, demonstrating broad functional group tolerance and scalability.
Technology Process of Trimethyl(trifluoromethyl)silane

There total 15 articles about Trimethyl(trifluoromethyl)silane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
With Tetrakis(dimethylamino)ethylen; In benzonitrile; at 20 ℃; for 1h;
DOI:10.1016/S0022-1139(00)83934-2
Guidance literature:
With magnesium; In tetrahydrofuran; ethylene dibromide; at 0 - 30 ℃; for 2h; Solvent; Inert atmosphere;
Refernces Edit

Reactions of difluoroenoxysilanes with glycosyl donors: Synthesis of difluoro-C-glycosides and difluoro-C-disaccharides

10.1002/1521-3765(20010216)7:4<903::AID-CHEM903>3.0.CO;2-M

The research focuses on the synthesis of difluoro-C-glycosides and difluoro-C-disaccharides through the reactions of difluoroenoxysilanes with glycosyl donors, such as acylglycosides and glycals. The study explores the influence of the substituent in the 2-position of the glycosyl donor on the reaction's regioselectivity and stereoselectivity. Key reactants include acylsilanes, trifluoromethyltrimethylsilane (TFMTMS), and various glycosyl donors. The methodology involves the preparation of difluoroenoxysilanes from acylsilanes and TFMTMS under fluoride activation, followed by glycosylation with glycosyl donors. Analyses used to characterize the products include nuclear magnetic resonance (NMR) spectroscopy, infrared (IR) spectroscopy, mass spectrometry (MS), and elemental analysis. The research also discusses the potential of these compounds as non-hydrolyzable glycoside mimics and their biochemical properties.

Mild and metal-free trifluoromethylation and pentafluoroethylation of gem-difluoroalkenes with TMSCF3 and TMSCF2CF3

10.1016/j.tet.2015.08.016

The study presents a direct and efficient method for the trifluoromethylation and pentafluoroethylation of 1,1-diaryl-2,2-difluoroethenes using TMSCF3 and TMSCF2CF3, respectively, in the presence of TBAF as a fluoride source, without the need for metal catalysts. The reactions were conducted under mild conditions and yielded a variety of monotrifluoromethylated, bistrifluoromethylated, monopentafluoroethylated, and bispentafluoroethylated products in fair to good yields. The chemicals used in the study include TMSCF3 (known as Ruppert-Prakash reagent), TMSCF2CF3, TBAF, and various 1,1-diaryl-2,2-difluoroethenes. These chemicals served the purpose of enabling the synthesis of complex organic molecules with fluorinated alkene structures, which are valuable in pharmaceuticals, agrochemicals, and material science due to their unique properties.

Fluoride-Induced Trifluoromethylation of Carbonyl Compounds with Trifluoromethyltrimethylsilane (TMS-CF3). A Trifluoromethide Equivalent

10.1021/ja00183a073

The study investigates the reactivity of the metal-oxo complex CP*~W=O, exploring its interactions with various substances. The complex undergoes 1,2-additions with both polar and nonpolar u bonds, such as H-H and H-SiMe3, leading to the formation of different tungsten derivatives. It also reacts with oxidizing agents like H2O2 and Me3CO2H, resulting in oxygen atom transfer and the formation of dioxo tungsten derivatives. Notably, the complex reacts with O2, leading to the insertion of an oxygen atom from O2 into a W-($-C,Me,) bond, forming (T$-C,M~,)W(=O),- (OC,Me,). The study highlights the potential of organotungsten derivatives in catalytic oxidation reactions. Additionally, the study explores the use of trifluoromethyltrimethylsilane (TMS-CF3) as a nucleophilic trifluoromethylating agent for carbonyl compounds, catalyzed by fluoride ions, resulting in the formation of trifluoromethylated siloxy adducts which can be hydrolyzed to alcohols.

Trifluoromethylation of Benzoic Acids: An Access to Aryl Trifluoromethyl Ketones

10.1021/acs.orglett.1c01720

The study presents an efficient method for the trifluoromethylation of benzoic acids using TMSCF3 (trimethylsilyl trifluoromethane) to produce aryl trifluoromethyl ketones. The reaction involves anhydrides as in situ activating reagents, with trifluoroacetic anhydride (TFAA) and 4-dimethylaminopyridine (DMAP) playing crucial roles in activating the carboxylic acids and facilitating nucleophilic addition. CsF (cesium fluoride) is used to enhance the yield of the desired products. The reaction is conducted in PhOMe (anisole) solvent under nitrogen at 120 °C for 15 hours. The study demonstrates a wide substrate scope, including various carboxylic acids with different functional groups, and shows high functional group tolerance. Notably, bioactive molecules such as adapalin, probenecid, and telmisartan can also be trifluoromethylated using this method, highlighting its potential in drug design and development. The reaction conditions are relatively mild, and the process is scalable, making it a practical and environmentally benign approach for synthesizing aryl trifluoromethyl ketones.

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