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900015

Sigma-Aldrich

Trimethylpentafluoroethylsilane

97%

Sinonimo/i:

(Pentafluoroethyl)trimethylsilane

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About This Item

Formula empirica (notazione di Hill):
C5H9F5Si
Numero CAS:
124898-13-1
Peso molecolare:
192.20
Numero MDL:
MFCD04116436
Codice UNSPSC:
12352101
ID PubChem:
329769760
NACRES:
NA.22

Saggio

97%

Forma fisica

liquid

Indice di rifrazione

n/D 1.325

Densità

1.095 g/mL

Stringa SMILE

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
MTPVUVINMAGMJL-UHFFFAOYSA-N

Descrizione generale

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

Applicazioni

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.

Note legali

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

Pittogrammi

FlameExclamation mark
GHS02,GHS07

Avvertenze

Danger

Indicazioni di pericolo

H225,H315,H319,H335

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

1.4 °F - closed cup - (calculated)

Punto d’infiammabilità (°C)

-17 °C - closed cup - (calculated)

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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)
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)
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

Contenuto correlato

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.

Il team dei nostri ricercatori vanta grande esperienza in tutte le aree della ricerca quali Life Science, scienza dei materiali, sintesi chimica, cromatografia, discipline analitiche, ecc..

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