(Trifluoromethyl)trimethylsilane

Bezeichnung:(Trifluoromethyl)trimethylsilane

CAS-Nr81290-20-2

Englisch Name:(Trifluoromethyl)trimethylsilane

CBNumberCB1386873

SummenformelC4H9F3Si

Molgewicht142.2

MOL-Datei81290-20-2.mol

(Trifluoromethyl)trimethylsilane physikalisch-chemischer Eigenschaften

Siedepunkt	54-55 °C (lit.)
Dichte	0.962 g/mL at 20 °C (lit.)
Dampfdruck	10.98 psi ( 55 °C)
Brechungsindex	n20/D 1.386
Flammpunkt	14 °F
storage temp.	2-8°C
Löslichkeit	sol THF, ether, CH2Cl2.
Aggregatzustand	Liquid
Wichte	0.962
Farbe	Clear colorless
Wasserlöslichkeit	Soluble in alcohol, THF, ether, dichloromethane, aromatic and aliphatic hydrocarbons. Soluble in water(with white smokes).
Sensitive	Moisture Sensitive
Hydrolytic Sensitivity	4: no reaction with water under neutral conditions
Merck	14,9683
BRN	4241868
Expositionsgrenzwerte	ACGIH: TWA 50 ppm; STEL 100 ppm (Skin) OSHA: TWA 200 ppm(590 mg/m3) NIOSH: IDLH 2000 ppm; TWA 200 ppm(590 mg/m3); STEL 250 ppm(735 mg/m3)
Stabilität	Volatile
InChIKey	MWKJTNBSKNUMFN-UHFFFAOYSA-N
CAS Datenbank	81290-20-2(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	F,Xi,Xn
R-Sätze:	11-36/37-19-36/37/38-22-40-14
S-Sätze:	16-33-39-26-36-29-36/37
RIDADR	UN 1993 3/PG 2
WGK Germany	3
F	10-21
Hazard Note	Flammable
TSCA	No
HazardClass	3
PackingGroup	II
HS Code	29319090

Gefahreninformationscode (GHS)

(Trifluoromethyl)trimethylsilane Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R11:Leichtentzündlich.
R36/37:Reizt die Augen und die Atmungsorgane.
R19:Kann explosionsfähige Peroxide bilden.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R22:Gesundheitsschädlich beim Verschlucken.
S-Sätze Betriebsanweisung:
S16:Von Zündquellen fernhalten - Nicht rauchen.
S33:Maßnahmen gegen elektrostatische Aufladungen treffen.
S39:Schutzbrille/Gesichtsschutz tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S29:Nicht in die Kanalisation gelangen lassen.
Chemische Eigenschaften
(Trifluoromethyl)trimethylsilane (TMSCF3) is a flammable colorless liquid with a boiling point of 54–55 °C, a flash point of –17 °C and density of 0.926 g/mL at 20 °C. It is a trifluoromethylation reagent used in nucleophilic addition reactions of aldehydes and ketones. It may be harmful if inhaled, swallowed, absorbed through skin and may cause respiratory tract, skin and eye irritation. TMSCF3 was firstly synthesized by Rupert in 1984 via the condensation reaction of CF3Br and TMSCl with (Et2N)3P.
Verwenden
Silicon-based fluorinating reagents for the efficient trifluoromethylation of carbonyls and ethylene diamines. Precursors used for metal-mediated trifluoromethylation of aromatic, heteroaromatic, vinyl substrates, etc.
Verwenden
TMSCF3 is versatile reagent for trifluoromethylation, such as transition-metal-catalyzed reaction, miscellaneous trifluoromethylation, and addition to carbonyl and imine groups. These reactions are extremely useful approaches in the pharmaceutical and agrochemical industry, because they enhance metabolic stability (metabolic blocking) and alter the compound properties (liphophilicity, binding selectivity).
synthetische
(Trifluoromethyl)trimethylsilane is prepared from trimethylsilyl chloride and bromotrifluoromethane in the presence of a phosphorus(III) reagent that serves as a halogen acceptor.
Allgemeine Beschreibung
Trimethyl(trifluoromethyl)silane (TMSCF₃) is also called as Ruppert-Prakash fluorination reagent. It is extensively used for the synthesis of trifluoromethyl-containing compounds.
Toxikologie
(Trifluoromethyl)trimethylsilane is classified as toxic and requires careful handling and safety protocols to minimize human exposure. Prolonged or repeated exposure can lead to various health problems such as skin, eye, and respiratory irritation.
läuterung methode
Purify it by distilling it from trap to trap in a vacuum of 20mm using a bath at 45o and Dry-ice/Me2CO bath for the trap. The liquid in the trap is then washed with ice cold H2O (3x), the top layer is collected, dried (Na2SO4), and the liquid is decanted and fractionated through a helices-packed column at atmospheric pressure. 1H, 1 3C, 1 9F, and 2 9Si NMR can be used for assessing the purity of fractions. [Ruppert et al. Tetrahedron Lett 25 2195 1984, Krishnamurti et al. J Org Chem 56 984 199, Beilstein 4 IV 3892.]

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