| Identification | More | [Name]
(Trifluoromethyl)trimethylsilane | [CAS]
81290-20-2 | [Synonyms]
RUPPERT'S REAGENT
TFMTMS
TMS-CF3
(TRIFLUOROMETHYL)TRIMETHYLSILANE
(TRIMETHYLSILYL)TRIFLUOROMETHANE
TRIMETHYL(TRIFLUOROMETHYL)SILANE
TTMS
(Trifluoromethyl)-trimethylsilan
Ruppert's
(Trifluoromethyl)trimethylsilane 0.5M solution in THF
TRIMETHYL(TRIFLUOROMETHYL)SILANE, 0.5M S OLUTION IN TETRAHYDROFURAN
Trimethyl(trifluoromethyl)silane solution
(Trifluoromethyl)trimethylsilane, 99%+
Ruppertreagent
Trifluoromethyltrimethylsilane0.5MinTHF
Trifluoromethyltrimethylsilane,min.97%
(Trifluoromethyl)trimethylsilane 0.5M solution in THF 98%
(Trifluoromethyl)trimethylsilane0.5MsolutioninTHF98%
(trifluromethyl)trimethylsilane
(Trifluoromethyl)trimethylsilane [Trifluoromethylating Reagent] | [Molecular Formula]
C4H9F3Si | [MDL Number]
MFCD00145454 | [Molecular Weight]
142.19 | [MOL File]
81290-20-2.mol |
| Chemical Properties | Back Directory | [Appearance]
clear colorless solution | [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
| [Fp ]
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 ]
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 Data | Back Directory | [Hazard Codes ]
F,Xi,Xn | [Risk Statements ]
R11:Highly Flammable.
R36/37:Irritating to eyes and respiratory system .
R19:May form explosive peroxides.
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S33:Take precautionary measures against static discharges .
S39:Wear eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S29:Do not empty into drains . | [RIDADR ]
UN 1993 3/PG 2
| [WGK Germany ]
3
| [F ]
10-21 | [Hazard Note ]
Flammable | [TSCA ]
No | [HazardClass ]
3 | [PackingGroup ]
II | [HS Code ]
29319099 |
| Hazard Information | Back Directory | [Chemical Properties]
clear colorless solution | [Physical properties]
bp 54–55 °C; d20 0.963 g cm?3 | [Uses]
Nucleophilic addition of the trifluoromethyl group to aldehydes and ketones.1 | [Uses]
Nucleophilic trifluoromethylating reagent. | [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. | [reaction suitability]
reaction type: C-C Bond Formation | [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.
| [Synthesis]
160 g of anhydrous toluene and 19.5 g (0.5 mol) of potassium metal were added to a 1000 mL three-necked flask and the apparatus was protected by argon. The temperature was raised to 55 °C, followed by the dropwise addition of a mixture of 104 g (1 mol) styrene and 161 g (1 mol) hexamethyldisilazane over about 30 minutes. The reaction was maintained for 2 hours until the potassium metal was completely dissolved and then cooled to room temperature to obtain a reaction solution. The reaction solution was cooled to -85 °C and maintained for 20 minutes. 81 g (0.75 mol) of trimethylchlorosilane was slowly added dropwise. Subsequently, trifluoromethane was passed into the reaction system and stopped when 35 g (0.5 mol) of trifluoromethane was passed. The reaction mixture was kept at -85°C for 1 hour and then slowly warmed up to room temperature. The reaction mixture was washed twice with water to ensure that all solids were dissolved and left to stratify. The organic layer was separated and distilled to give a final 64 g (88% yield) of trifluoromethyltrimethylsilane. | [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.] | [References]
[1] Patent: CN106117258, 2016, A. Location in patent: Paragraph 0024; 0025; 0026; 0027; 0028; 0029-0035
[2] Science, 2012, vol. 338, # 6112, p. 1324 - 1327
[3] Patent: US2014/66640, 2014, A1. Location in patent: Paragraph 0057
[4] Patent: WO2017/223406, 2017, A1. Location in patent: Paragraph 00157; 00159; 00160 |
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