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About This Item
Linear Formula:
(CH3)3SiCF3
CAS Number:
Molecular Weight:
142.19
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
4241868
InChI
1S/C4H9F3Si/c1-8(2,3)4(5,6)7/h1-3H3
SMILES string
C[Si](C)(C)C(F)(F)F
InChI key
MWKJTNBSKNUMFN-UHFFFAOYSA-N
form
liquid
reaction suitability
reaction type: C-C Bond Formation
IVD
for in vitro diagnostic use
concentration
2 M in THF
refractive index
n20/D 1.386
density
0.91 g/mL at 20 °C
functional group
fluoro
Quality Level
General description
Trimethyl(trifluoromethyl)silane (TMSCF3) is also called as Ruppert-Prakash fluorination reagent. It is extensively used for the synthesis of trifluoromethyl-containing compounds.
Application
Reactant for:
- Silver-mediated C-H trifluoromethylation of arenes
- Preparation of trifluoromethyl ketone analog of L-arginine having contrasting inhibitory activity against human arginase I and histone deacetylase 8
- Organocatalyzed regio- and enantioselective allylic trifluoromethylation of Morita-Baylis-Hillman adducts
- Palladium-catalyzed oxidative trifluoromethylation of indoles
- Preparation of 5-HT1A antagonists
- Used as difluorocarbene source
TMSCF3 can be used as a reagent for:
It can also be used in trifluoromethylation of:
- Conversion of aromatic aldehydes to difluoromethylated products.
- C-H trifluoromethylation of arenes, terminal alkynes, tertiary amines, heteroarenes, allylic, and terminal alkenes using metal catalyst or metal free oxidative trifluoromethylation reaction.
It can also be used in trifluoromethylation of:
- Non-activated aldimines.
- Heterocumulenes.
- Azomethine imines.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3
target_organs
Respiratory system
supp_hazards
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
1.4 °F
flash_point_c
-17 °C
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
危险化学品
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Oxidative trifluoromethylation and trifluoromethylthiolation reactions using (trifluoromethyl) trimethylsilane as a nucleophilic CF3 source
Chu L and Qing F-L
Accounts of Chemical Research, 47(5), 1513-1522 (2014)
Palladium-Catalyzed Oxidative Trifluoromethylation of Indoles at Room Temperature
Mu X, et al.
Chemistry?A European Journal , 17(22), 6039-6042 (2011)
Organocatalyzed Regio-and Enantioselective Allylic Trifluoromethylation of Morita-Baylis-Hillman Adducts Using Ruppert-Prakash Reagent
Furukawa T, et al.
Organic Letters, 13(15), 3972-3975 (2011)
Trifluoromethylation of heterocumulenes with trimethyl (trifluoromethyl) silane in the presence of fluoride ions: synthesis of trifluoroacetamides and trifluorothioacetamides from isocyanates and isothiocyanates
Kirij NV, et al.
Tetrahedron Letters, 42(46), 8181-8183 (2001)
Nucleophilic difluoromethylation of aromatic aldehydes using trimethyl (trifluoromethyl) silane (TMSCF3)
Krishnamoorthy S, et al.
Journal of Fluorine Chemistry, 208, 10-14 (2018)
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