(Trifluoromethyl)trimethylsilane Property

Boiling point:

54-55 °C (lit.)

Density 

0.962 g/mL at 20 °C (lit.)

vapor pressure 

10.98 psi ( 55 °C)

refractive index 

n20/D 1.386

Flash point:

14 °F

storage temp. 

2-8°C

solubility 

sol THF, ether, CH2Cl2.

form 

Liquid

color 

Clear colorless

Specific Gravity

0.962

Water Solubility 

Soluble in alcohol, THF, ether, dichloromethane, aromatic and aliphatic hydrocarbons. Soluble in water(with white smokes).

Hydrolytic Sensitivity

4: no reaction with water under neutral conditions

Sensitive 

Moisture Sensitive

Merck 

14,9683

BRN 

4241868

Exposure limits

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)

Stability:

Volatile

InChIKey

MWKJTNBSKNUMFN-UHFFFAOYSA-N

CAS DataBase Reference

81290-20-2(CAS DataBase Reference)

Safety

Hazard Codes 

F,Xi,Xn

Risk Statements 

11-36/37-19-36/37/38-22-40-14

Safety Statements 

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H261In contact with water releases flammable gas

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P223Keep away from any possible contact with water, because of violent reaction and possible flash fire.

P231+P232Handle under inert gas. Protect from moisture.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

(Trifluoromethyl)trimethylsilane Chemical Properties,Usage,Production

Chemical Properties

(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.

Uses

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).

Uses

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.

Preparation

(Trifluoromethyl)trimethylsilane is prepared from trimethylsilyl chloride and bromotrifluoromethane in the presence of a phosphorus(III) reagent that serves as a halogen acceptor.

General Description

Trimethyl(trifluoromethyl)silane (TMSCF₃) is also called as Ruppert-Prakash fluorination reagent. It is extensively used for the synthesis of trifluoromethyl-containing compounds.

Toxicology

(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.

Purification Methods

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.]