Trimethyl(trifluoromethyl)silane

Base Information

• 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

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

Chemical Property of Trimethyl(trifluoromethyl)silane

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): F,Xn,Xi
• 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
• Uses: TMSCF3 is versatile reagent for trifluoromethylation, such as transition-metal-catalyzed reaction, miscellaneous trifluoromethylation, and addition to carbonyl and imine groups. These reactions are extremely useful approaches in the pharmaceutical and agrochemical industry, because they enhance metabolic stability (metabolic blocking) and alter the compound properties (liphophilicity, binding selectivity).

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:

Reference yield: 95.0%

chloro-trimethyl-silane (75-77-4) + Bromotrifluoromethane (75-63-8) + hexaethylphosphoric triamide (2283-11-6) → (trifluoromethyl)trimethylsilane (81290-20-2) + (N(C2H5)2)3PClBr (89217-83-4)

Guidance literature:

In dichloromethane;

DOI:10.1016/S0040-4039(01)80208-2

Reference yield: 94.0%

chloro-trimethyl-silane (75-77-4) + iodotrifluoromethane (2314-97-8,263005-66-9) → (trifluoromethyl)trimethylsilane (81290-20-2)

Guidance literature:

With Tetrakis(dimethylamino)ethylen; In benzonitrile; at 20 ℃; for 1h;

DOI:10.1016/S0022-1139(00)83934-2

Reference yield: 93.8%

chloro-trimethyl-silane (75-77-4) + Bromotrifluoromethane (75-63-8) → (trifluoromethyl)trimethylsilane (81290-20-2)

Guidance literature:

With magnesium; In tetrahydrofuran; ethylene dibromide; at 0 - 30 ℃; for 2h; Solvent; Inert atmosphere;

upstream raw materials:

chloro-trimethyl-silane

Bromotrifluoromethane

iodotrifluoromethane

1,1,1,2,2,2-hexamethyldisilane

Downstream raw materials:

Phenyl-(2,2,2-trifluoro-1-furan-2-yl-ethyl)-amine

2,2,2-Trifluoroacetophenone

trimethyl[2,2,2-trifluoro-1-phenyl-1-(trifluoromethyl)ethoxy]silane

trimethyl[(2,2,2-trifluoro-1-phenylethoxy)]silane

Refernces

• 1、 Aymard, Frederic,Nedelec, Jean-Yves,Perichon, Jacques. "An efficient inexpensive electrochemical preparation of Ruppert's reagent". . p. 8623 - 8624. Retrieved 1994.
• 2、 -. "Preparation method of trifluoromethyltrimethylsilane". Paragraph 0040-0063. . Retrieved 2021/07/14.
• 3、 Geri, Jacob B.,Wade Wolfe, Michael M.,Szymczak, Nathaniel K.. "Borazine-CF3? Adducts for Rapid, Room Temperature, and Broad Scope Trifluoromethylation". supporting information. p. 1381 - 1385. Retrieved 2018/01/15.