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Merck
CN

367737

Trimethyl(trifluoromethyl)silane solution

0.5 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
PubChem Substance ID:
24862831
UNSPSC Code:
12352101
Beilstein/REAXYS Number:
4241868
MDL number:
MFCD00145454

Key Documents

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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

vapor pressure

10.98 psi ( 55 °C), 2.8 psi ( 20 °C)

form

liquid

concentration

0.5 M in THF

bp

40 °C

density

0.895 g/mL at 25 °C

Application

Nucleophilic addition of the trifluoromethyl group to aldehydes and ketones.
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

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

supp_hazards

EUH019

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

1.4 °F - closed cup

flash_point_c

-17 °C - closed cup

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
82596DM
80396DM
13218MH
00210EE
18426LO

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Journal of the American Chemical Society, 111, 393-393 (1989)
J W Skiles et al.
Journal of medicinal chemistry, 35(4), 641-662 (1992-02-21)
A series of tripeptides possessing trifluoromethyl or aryl ketone residues at P1 were prepared and evaluated both in vitro and in vivo as potential inhibitors of human leukocyte elastase (HLE). Tripeptides containing non naturally occurring N-substituted glycine residues at the
The Journal of Organic Chemistry, 57, 1124-1124 (1992)
G K Surya Prakash et al.
The Journal of organic chemistry, 71(18), 6806-6813 (2006-08-26)
Organofluorine compounds are becoming increasingly important in different fields, such as material science, agro chemistry, and the pharmaceutical industry. Nucleophilic trifluoromethylation is one of the widely used methods to incorporate a trifluoromethyl moiety into organic molecules. We have carried out

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