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488712

Sigma-Aldrich

Trimethyl(trifluoromethyl)silane

99%

Sinonimo/i:

(Trifluoromethyl)trimethylsilane, Ruppert’s Reagent, TFMTMS

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About This Item

Formula condensata:
(CH3)3SiCF3
Numero CAS:
81290-20-2
Peso molecolare:
142.19
Beilstein:
4241868
Numero MDL:
MFCD00145454
Codice UNSPSC:
12352101
ID PubChem:
24872418
NACRES:
NA.22

Livello qualitativo

200

Saggio

99%

Impiego in reazioni chimiche

reaction type: C-C Bond Formation

P. eboll.

54-55 °C (lit.)

Densità

0.962 g/mL at 20 °C (lit.)

Gruppo funzionale

fluoro

Temperatura di conservazione

2-8°C

Stringa SMILE

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

InChI

1S/C4H9F3Si/c1-8(2,3)4(5,6)7/h1-3H3
MWKJTNBSKNUMFN-UHFFFAOYSA-N

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Applicazioni

Trimethyl(trifluoromethyl)silane can be used as a trifluoromethylating agent in the following processes:
  • Conversion of N-(tert-butylsulfinyl)-imines to trifluoromethylated amines
  • Conversion of trans-enones to trans-α-trifluoromethyl silyl ethers
  • Trifluoromethylation of azomethine imines
  • Conversion of H-phosphonates to CF3-phosphonates
  • Nucleophilic addition of the trifluoromethyl group to aldehydes and ketones.

Pittogrammi

Flame
GHS02

Avvertenze

Danger

Indicazioni di pericolo

H225,H261

Classi di pericolo

Flam. Liq. 2 - Water-react 2

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

1.4 °F - closed cup

Punto d’infiammabilità (°C)

-17 °C - closed cup

Dispositivi di protezione individuale

Eyeshields, Faceshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
BCCG6515
BCCF0617
BCCB4821
BCBW9275
BCBV1411

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Craig P Johnston et al.
Journal of the American Chemical Society, 140(35), 11112-11124 (2018-08-07)
The mechanism of CF3 transfer from R3SiCF3 (R = Me, Et, iPr) to ketones and aldehydes, initiated by M+X- (<0.004 to 10 mol %), has been investigated by analysis of kinetics (variable-ratio stopped-flow NMR and IR), 13C/2H KIEs, LFER, addition
Catalytic enantioselective trifluoromethylation of azomethine imines with trimethyl (trifluoromethyl) silane
Kawai H, et al.
Angewandte Chemie (International Edition in English), 121(34), 6442-6445 (2009)
Peter T Kaplan et al.
Beilstein journal of organic chemistry, 13, 2297-2303 (2017-11-29)
A number of copper reagents were compared for their effectiveness in trifluoromethylating 4-iodobiphenyl, 4-iodotoluene, and 2-iodotoluene. Yields over time were plotted in order to refine our understanding of each reagent performance, identify any bottlenecks, and provide more insight into the
Stereoselective Nucleophilic Trifluoromethylation of N?(tert?Butylsulfinyl) imines by Using Trimethyl (trifluoromethyl) silane.
Prakash G K, et al.
Angewandte Chemie (International Edition in English), 113(3), 609-610 (2001)
CsF-catalyzed nucleophilic trifluoromethylation of trans-enones with trimethyl (trifluoromethyl) silane: A facile synthesis of trans-?-trifluoromethyl allylic alcohols.
Singh R P, et al.
Organic Letters, 1(7), 1047-1049 (1999)
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Articoli

Reagents for C–C Bond Formation

We carry a large variety of electrophiles and nucleophiles that are widely used in C–C bond-forming reactions. This group of products contains many organometallic reagents as well as commonly-used alkylating and acylating reagents.

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