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CAS RN: 81290-20-2 | 产品编码: T1570
(Trifluoromethyl)trimethylsilane [Trifluoromethylating Reagent]
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技术规格
| Appearance | Colorless to Light yellow clear liquid |
| Purity(GC) | min. 97.0 % |
物性（参考值）
| 沸点 | 55 °C |
| 闪点 | -32 °C |
| 比重 | 0.96 |
| 折射率 | 1.33 |
GHS
| 象形图 |
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| 信号词 | Danger |
| 危险性说明 | H225 : Highly flammable liquid and vapor. |
| 防范说明 | P501 : Dispose of contents/ container to an approved waste disposal plant. P240 : Ground/bond container and receiving equipment. P210 : Keep away from heat/sparks/open flames/hot surfaces. No smoking. P233 : Keep container tightly closed. P243 : Take precautionary measures against static discharge. P241 : Use explosion-proof electrical/ ventilating/ lighting/ equipment. P242 : Use only non-sparking tools. P280 : Wear protective gloves/ eye protection/ face protection. P370 + P378 : In case of fire: Use dry sand, dry chemical or alcohol-resistant foam to extinguish. P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water/shower. P403 + P235 : Store in a well-ventilated place. Keep cool. |
相关法规
运输信息
| UN编号 | UN1993 |
| 类别 | 3 |
| 包装类别 | II |
| HS编码* | 2931.90-000 |
应用
Synthesis of Trifluoromethylketones from Weinreb Amides
Typical Procedure:
To a 50 mL round bottom flask equipped with a stir bar is added CsF (0.1512 g, 1.0 mmol, 0.2 eq.). Toluene (2.5 mL) is added to the flask, followed by 4-(tert-butyl)-N-methoxy-N-methylbenzamide (1.11 g, 5.0 mmol, 1 eq.). The flask is sealed with a septum equipped with an inlet needle as an exit valve. The flask is cooled to 0 °C for 10 minutes. Once cooled, TMSCF3 (1.42 g, 10.0 mmol, 2 eq.) is added to the reaction mixture dropwise over a period of ≈ 10 minutes. After completion of addition, the reaction mixture is allowed to stir at 0 °C for 10 minutes. The cooling bath is removed and the reaction mixture is allowed to stir at room temperature overnight. (Upon reaching room temperature, the reaction occurs and is mildly exothermic and gas is evolved.) Reaction progress is monitored by 1H NMR.
Once complete conversion to the silylated intermediate is confirmed, water (5 mL) followed by TBAF (5 mL, 1 M in THF, 1 eq.) is added to the reaction flask. The flask is equipped with a reflux condenser, open to air. The contents are then heated to 50 °C, and allowed to stir at that temperature for 2 hours. Once cooled to room temperature, the reaction mixture is diluted with Et2O (≈ 30 mL), and transferred to a separatory funnel. The organic layer is washed with deionized water (3 × 30 mL), followed with a brine solution (1 × 30 mL). The organic layer is dried with Na2SO4 and the solvent is removed in vacuo by rotary evaporation to yield crude trifluoromethylketone. Further purification is accomplished by flash chromatography (hexane : EtOAc = 8 : 2) to produce the pure CF3 ketone as an orange solid (0.935 g, Y. 81%).
To a 50 mL round bottom flask equipped with a stir bar is added CsF (0.1512 g, 1.0 mmol, 0.2 eq.). Toluene (2.5 mL) is added to the flask, followed by 4-(tert-butyl)-N-methoxy-N-methylbenzamide (1.11 g, 5.0 mmol, 1 eq.). The flask is sealed with a septum equipped with an inlet needle as an exit valve. The flask is cooled to 0 °C for 10 minutes. Once cooled, TMSCF3 (1.42 g, 10.0 mmol, 2 eq.) is added to the reaction mixture dropwise over a period of ≈ 10 minutes. After completion of addition, the reaction mixture is allowed to stir at 0 °C for 10 minutes. The cooling bath is removed and the reaction mixture is allowed to stir at room temperature overnight. (Upon reaching room temperature, the reaction occurs and is mildly exothermic and gas is evolved.) Reaction progress is monitored by 1H NMR.
Once complete conversion to the silylated intermediate is confirmed, water (5 mL) followed by TBAF (5 mL, 1 M in THF, 1 eq.) is added to the reaction flask. The flask is equipped with a reflux condenser, open to air. The contents are then heated to 50 °C, and allowed to stir at that temperature for 2 hours. Once cooled to room temperature, the reaction mixture is diluted with Et2O (≈ 30 mL), and transferred to a separatory funnel. The organic layer is washed with deionized water (3 × 30 mL), followed with a brine solution (1 × 30 mL). The organic layer is dried with Na2SO4 and the solvent is removed in vacuo by rotary evaporation to yield crude trifluoromethylketone. Further purification is accomplished by flash chromatography (hexane : EtOAc = 8 : 2) to produce the pure CF3 ketone as an orange solid (0.935 g, Y. 81%).
References
应用
Nucleophilic Trifluoromethylation
Reference
应用
Difluorocarbene Precursor
Reference
- Synthesis of gem-difluorinated cyclopropanes and cyclopropenes: trifluoromethyltrimethylsilane as a difluorocarbene source
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