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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
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
57653455
MDL number:
MFCD00145454
Beilstein/REAXYS Number:
4241868
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form

liquid

Quality Segment

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, silyl

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

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

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.

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

Hazard Classifications

Acute Tox. 4 Oral - Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - STOT SE 3 - Water-react. 2

target_organs

Central nervous system, Respiratory system

Storage Class

4.3 - Hazardous materials which set free flammable gases upon contact with water

signalword

Danger

supp_hazards

EUH019

flash_point_f

1.4 °F

flash_point_c

-17 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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