Skip to Content
Merck
All Photos(1)

Key Documents

91862

Sigma-Aldrich

Trimethyl(trifluoromethyl)silane solution

2 M in THF

Synonym(s):

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

Sign Into View Organizational & Contract Pricing


About This Item

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

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

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

Looking for similar products? Visit Product Comparison Guide

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

Hazard Classifications

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

Target Organs

Respiratory system

Supplementary Hazards

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
Palladium-Catalyzed Oxidative Trifluoromethylation of Indoles at Room Temperature
Mu X, et al.
Chemistry?A European Journal , 17(22), 6039-6042 (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)
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)
Recent advances in transition-metal-catalyzed trifluoromethylation and related transformations
Chen P and Liu G
Synthesis, 45(21), 2919-2939 (2013)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service