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Merck
CN

91862

Trimethyl(trifluoromethyl)silane solution

2 M in THF

Synonym(s):

(Trifluoromethyl)trimethylsilane, Ruppert′s reagent, Ruppert-Prakash reagent, TFMTMS, Trifluoromethyltrimethylsilane

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About This Item

Linear Formula:
(CH3)3SiCF3
CAS Number:
81290-20-2
Molecular Weight:
142.19
Beilstein:
4241868
MDL number:
MFCD00145454
UNSPSC Code:
12352101
PubChem Substance ID:
57653455
NACRES:
NA.22

Key Documents

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form

liquid

Quality Level

100

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

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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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:
  • 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.

Signal Word

Danger

Hazard Statements

H225,H302,H319,H335,H351

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH019

Storage Class Code

3 - Flammable liquids

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
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Certificates of Analysis (COA)

Lot/Batch Number
BCCF7475
BCBV6199
BCBQ2152V
BCBK6529V
BCBH7401V

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Recent advances in transition-metal-catalyzed trifluoromethylation and related transformations
Chen P and Liu G
Synthesis, 45(21), 2919-2939 (2013)
Trifluoromethylation of non-activated aldimines with trimethyl (trifluoromethyl) silane in the presence of tetramethylammonium fluoride: A closer look into the reaction route
Kirij NV, et al.
Journal of Fluorine Chemistry, 129(1), 14-21 (2008)
Catalytic enantioselective trifluoromethylation of azomethine imines with trimethyl (trifluoromethyl) silane
Kawai H, et al.
Angewandte Chemie (International Edition in English), 48(34), 6324-6327 (2009)
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)
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)
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