(Trifluoromethyl)trimethylsilane

Synonym
Product Category
Product Code
CAS Number
MDL Number
Pubchem SID
Reaxys RN
(Trimethyl)trifluoromethylsilane, Ruppert’s Reagent, TFMTMS,CF3TMS
Trifluoromethylating Reagents,Difluorocarbene Precursors 
KUMI3F01
81290-20-2
MFCD00145454
24872418
4241868
image-155171-Trimethyl(trifluoromethyl)silane_reagent.png
Chemical Name
Molecular Formula
Molecular Weight
Assay(Analysis Method)
Appearance
Boiling  Point
Flash Point
Packaging
Storage
(Trifluoromethyl)trimethylsilane
C4H9F3Si
140.20
≥99.0% (GC)
Colorless to Light yellow Liquid
54-55ºC(lit.)
-17ºC(closed cup)
5g,10g,50g,100g,500g,1kg and 25kg
Store locked-up, in a cool, well-ventilated place
1.Nucleophilic Trifluoromethylation
1) Aldehydes and Ketones: 
Synthetic methods and reactions. 141. Fluoride-induced trifluoromethylation of carbonyl compounds with trifluoromethyltrimethylsilane (TMS-CF3). A trifluoromethide equivalent. [1]
A Weinreb amide approach to the synthesis of trifluoromethylketones. [2]
2) Enones:
Trans enones react with CF3-TMS in the presence of a catalytic amount of cesium fluoride to give trifluoromethylated allylic alcohols. [3]
3) Esters:
Esters react with CF3-TMS in the presence of a stoichiometric amount of F- to give the corresponding trifluoromethylketones. [4]
4) Aromatics:
The transient trifluoromethylcopper species is generated in situ from CF3-TMS in the presence of cuprous iodide and potassium fluoride; reaction with aryl iodide gives trifluoromethylated aryl compounds. [5]
5) Alkyl Iodides:
Silver-mediated fluorination of alkyl iodides with TMSCF3 as the fluorinating agent. [6]
6) Convenient Source of CF2=CF2:
TMSCF3 as a Convenient Source of CF2=CF2 for Pentafluoroethylation, (Aryloxy)tetrafluoroethylation, and Tetrafluoroethylation. [7]
7) Miscellaneous Trifluoromethylations of Carbohydrates:
Trifluoromethylation of 3-oxo-glucose proceeds with CF3-TMS and gives the L-allo isomer in 100% selectivity, although CF3MgBr gives the L-allo and D-gluco isomers in the ratio of 75:25, respectively. [8]
8) Stereoselective Trifluoromethylation of Secondary Propargyl Sulfonates:
Copper-Catalyzed Highly Stereoselective Trifluoromethylation and Difluoroalkylation of Secondary Propargyl Sulfonates. [9]
2.Difluorocarbene Precursor
Synthesis of gem-difluorinated cyclopropanes and cyclopropenes: trifluoromethyltrimethylsilane as a difluorocarbene source. [10]
2.Pentafluoroethylation Precursor
From C1 to C2: TMSCF3 as an Efficient Precursor for Pentafluoroethylation. [11]
References:
[1] G.K.S. Prakash, et al, J.Am.Chem. Soc, 111, 393(1989).
[2] D.M.Rudzinski, et al, Chem.Commun.2012,48,9610.
[3] R.P. Singh, et al, Org. Lett. 1. 1047(1999).
[4] J.Wiedemann, et al, Angew. Chem. Int.Ed.,37.820(1998).
[5] T.Fuchikami, et al, JP 1991-218325.
[6] L.Wang, et al, Org. Chem. Front., 2017, Advance Article.
[7] L. Li, et al, Angew. Chem. Int. Ed., 2017, 56, pp 1-6.
[8] S.Lavaire, et al, Tetrahedron Asymmetry, 9,213(1998).
[9] X.Gao, et al, Angew. Chem. Int. Ed. Engl., 2018, 57(12), pp 3187-3191.
[10] F.Wang, et al, Angew.Chem. Int.50.7153(2011).
[11] Q.Xie, et al, Angew. Chem. Int. Ed. Engl., 2018.
Signal Word
Hazard Statements
Precautionary Statements
HS Code
RIDADR
Legal Information
Danger
H225
P210
2931.90.9010
UN 1993 BF 3/PG II

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