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900015

Sigma-Aldrich

Trimethylpentafluoroethylsilane

97%

Synonyme(s) :

(Pentafluoroethyl)trimethylsilane

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About This Item

Formule empirique (notation de Hill):
C5H9F5Si
Numéro CAS:
124898-13-1
Poids moléculaire :
192.20
Numéro MDL:
MFCD04116436
Code UNSPSC :
12352101
ID de substance PubChem :
329769760
Nomenclature NACRES :
NA.22

Pureté

97%

Forme

liquid

Indice de réfraction

n/D 1.325

Densité

1.095 g/mL

Chaîne SMILES 

C[Si](C)(C)C(F)(F)C(F)(F)F

InChI

1S/C5H9F5Si/c1-11(2,3)5(9,10)4(6,7)8/h1-3H3

Clé InChI

MTPVUVINMAGMJL-UHFFFAOYSA-N

Description générale

Trimethylpentafluoroethylsilane ((Pentafluoroethyl)trimethylsilane) is a perfluoroalkylsilane. Alkyl triflates undergo nucleophilic pentafluoroethylation with trimethylpentafluoroethylsilane to form the corresponding pentafluoroethylated alkanes.

Application

Trimethylpentafluoroethylsilane ((Pentafluoroethyl)trimethylsilane) may be used as a perfluoroalkylating reagent for the synthesis of the following quinoline derivatives:
  • 5-bromo-2-(perfluoroethyl)quinoline
  • 8-methoxy-2-(perfluoroethyl)quinoline
  • 1-(perfluoroethyl)isoquinoline
  • 8-(tert-butoxy)-5,7-dichloro-2-(perfluoroethyl)quinolone
It may also be used in the synthesis of pentafluoroethylcyclohexanes.
Trimethylpentafluoroethylsilane has been reported as a Ruppert-Prakash type reagent for the addition of pentafluoroethane. Recent report by Larionov and coworkers displayed the feasibility of adding pentrafluoroethane to N-heterocycles under basic conditions.

Informations légales

Synthetic and mechanistic aspects of the regioselective base-mediated reaction of perfluoroalkyl- and perfluoroarylsilanes with heterocyclic N-oxides

Pictogrammes

FlameExclamation mark
GHS02,GHS07

Mention d'avertissement

Danger

Mentions de danger

H225,H315,H319,H335

Classification des risques

Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

1.4 °F - closed cup - (calculated)

Point d'éclair (°C)

-17 °C - closed cup - (calculated)

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

Experimental determination of the conformational free energies (A values) of fluorinated substituents in cyclohexane by dynamic 19 F NMR spectroscopy. Part 2. Extension to fluoromethyl, difluoromethyl, pentafluoroethyl, trifluoromethylthio and trifluoromethoxy groups.
Carcenac Y, et al.
New. J. Chem., 30(3), 447-457 (2006)
A Facile New Method for the Two-step Substitution of Hydroxy Groups in Primary Alcohols for Trifluoromethyl and Pentafluoroethyl Moieties.
Sevenard DV, et al.
Synlett, 2001(03), 0379-0381 (2001)
David E Stephens et al.
Organic & biomolecular chemistry, 12(32), 6190-6199 (2014-07-06)
The scope and mechanistic implications of the direct transformation of heterocyclic N-oxides to 2-trifluoromethyl-, and related perfluoroalkyl- and perfluoroaryl-substituted N-heterocycles has been studied. The reaction is effected by perfluoroalkyl- and perfluorophenyltrimethylsilane in the presence of strong base. In situ displacement

Contenu apparenté

Hu Group – Professor Product Portal

The major research interests of Prof. Jinbo Hu's lab include the development of new fluorination reagents and reactions, especially the difluoromethylation, difluoromethylenation, and monofluoromethylation methods.

Notre équipe de scientifiques dispose d'une expérience dans tous les secteurs de la recherche, notamment en sciences de la vie, science des matériaux, synthèse chimique, chromatographie, analyse et dans de nombreux autres domaines..

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